Abstract
In this chapter, the recent developments of facile nitrile synthesis via N atom incorporation are summarized. Simple hydrocarbons, such as alkenes, and alkynes, have been converted to nitriles through C–H/C–C bond cleavage. Mechanistic studies and investigations of substrate scope in this nitrogenation strategy exhibit its broad application in chemistry community.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Bunch AW (1998) Nitriles. In: Rehm HJ, Reed G (eds) Biotechnology: biotransformations I, vol 8a, 2nd edn. Wiley-VCH Verlag GmbH, Weinheim
Kleemann A, Engel J, Kutscher B, Reichert D (2001) Pharmaceutical substances: syntheses, patents, applications, 4th edn. Georg Thieme, Stuttgart
Wang M-X (2015) Enantioselective biotransformations of nitriles in organic synthesis. Acc Chem Res 48(3):602–611
Kurono N, Ohkuma T (2016) Catalytic asymmetric cyanation reactions. ACS Catal 6(2):989–1023
Ellis GP, Romney-Alexander TM (1987) Cyanation of aromatic halides. Chem Rev 87(4):779–794
Wang T, Jiao N (2014) Direct approaches to nitriles via highly efficient nitrogenation strategy through C–H or C–C bond cleavage. Acc Chem Res 47(4):1137–1145
Liang Y, Liang Y-F, Jiao N (2015) Cu- or Fe-catalyzed C–H/C–C bond nitrogenation reactions for the direct synthesis of N-containing compounds. Org Chem Front 2(4):403–415
Hodgson HH (1947) The Sandmeyer reaction. Chem Rev 40(2):251–277
Cowdrey WA, Davies DS (1952) Sandmeyer and related reactions. Q Rev (Lond) 6:358–379
Wulfman DS (1978) Synthetic applications of diazonium ions. In: Patai S (ed) The chemistry of diazonium and diazo groups, Part 1. Wiley, London, pp 247–339
Galli C (1988) Radical reactions of arene diazonium ions: an easy entry into the chemistry of the aryl radical. Chem Rev 88(5):765–792
Merkushev EB (1988) Advances in the synthesis of iodo aromatic compounds. Synthesis 12:923–937
Bohlmann R (1991) Synthesis of halides. Comp Org Synth 6:203–223 (Trost BM, Fleming I (eds); Pergamon, Oxford)
Koelsch CF, Whitney AG (1941) The Rosenmund–von Braun nitrile synthesis. J Org Chem 06(6):795–803
Kim J, Stahl SS (2013) Cu/nitroxyl-catalyzed aerobic oxidation of primary amines into nitriles at room temperature. ACS Catal 3(7):1652–1656
Dennis WE (1970) Nitrile synthesis. The dehydration of amides by silazanes, chlorosilanes, alkoxysilanes, and aminosilanes. J Org Chem 35(10):3253–3255
Singh MK, Lakshman MK (2009) A simple synthesis of nitriles from aldoximes. J Org Chem 74(8):3079–3084
Wolff H (1946) Schmidt reaction. Org React 3(8):307–336
Smith PAS (1963) Rearrangements involving migration to an electron-deficient nitrogen or oxygen. In: Mayo P (ed) Molecular rearrangements, vol 1. Wiley, New York, pp 457–591
Shioiri T (1991) Degradation reactions. Comp Org Synth 6:795–828 (Trost BM, Fleming I (eds); Pergamon, Oxford)
Kim J, Chang S (2010) A new combined source of “CN” from N,N-dimethylformamide and ammonia in the palladium-catalyzed cyanation of aryl C–H bonds. J Am Chem Soc 132(30):10272–10274
Kim S, Choi J, Shin K, Chang S (2012) Copper-mediated sequential cyanation of aryl C–B and arene C–H bonds using ammonium iodide and DMF. J Am Chem Soc 134(5):2528–2531
Ren X, Chen J, Chen F, Cheng J (2011) The palladium-catalyzed cyanation of indole C–H bonds with the combination of NH4HCO3 and DMSO as a safe cyanide source. Chem Commun 47:6725–6727
Koldobskii GI, Ostrovskii VA, Gidaspov BV (1978) Schmidt reaction with aldehydes and carboxylic acids. Russ Chem Rev 47(11):1084–1094
Schmidt KF (1924) Über den Imin-Rest. Ber Dtsch Chem Ges 57(4):704–706
Schmidt KF (1923) Angew Chem 36:511
Beckwith ALJ (1970) Synthesis of amides. In: Zabicky (ed) Chemistry amides. Wiley, New York, pp 73–185
Koldobskii GI, Tereshchenko GF, Gerasimova ES, Bagal LI (1971) Schmidt reaction with ketones. Russ Chem Rev 40(10):835–846
Krow GR (1981) Nitrogen insertion reactions of bridged bicyclic ketones. Regioselective lactam formation. Tetrahedron 37(7):1283–1307
Pearson WH (1996) Aliphatic azides as Lewis bases. Application to the synthesis of heterocyclic compounds. J Heterocycl Chem 33(5):1489–1496
Vogler EA, Hayes JM (1979) Carbon isotopic fractionation in the Schmidt decarboxylation: evidence for two pathways to products. J Org Chem 44(21):3682–3686
Richard JP, Amyes TL, Lee Y-G, Jagannadham V (1994) Demonstration of the chemical competence of an iminodiazonium ion to serve as the reactive intermediate of a Schmidt reaction. J Am Chem Soc 116(23):10833–10834
Kaye PT, Mphahlele MJ, Brown ME (1995) Benzodiazepine analogs. Part 9. Kinetics and mechanism of the azidotrimethylsilane-mediated Schmidt reaction of flavanones. J Chem Soc Perkin Trans 2(4):835–838
McEwen WE, Conrad WE, VanderWerf CA (1952) The Schmidt reaction applied to aldehydes and epoxides. J Am Chem Soc 74(5):1168–1171
Schuerch C (1948) Preparation of vanillonitrile and vanillic acid from vanillin. J Am Chem Soc 70(6):2293–2294
Rokade BV, Prabhu JR (2012) Chemoselective Schmidt reaction mediated by triflic acid: selective synthesis of nitriles from aldehydes. J Org Chem 77(12):5364–5370
Nimnual P, Tummatorn J, Thongsornkleeb C, Ruchirawat S (2015) Utility of nitrogen extrusion of azido complexes for the synthesis of nitriles, benzoxazoles, and benzisoxazoles. J Org Chem 80(17):8657–8667
Kagarlitskii AD, Suvorov BV, Rafikov SR (1959) Ammonolysis of benzaldehyde on mixed oxide catalysts. Zhurnal Prikladnoĭ Khimii (Sankt-Peterburg, Russian Federation) 32:388–391
Iwahara H, Kushida T, Yamaguchi S (2016) A planarized 9-phenylanthracene: a simple electron-donating building block for fluorescent materials. Chem Commun 52(6):1124–1127
Mistry SN, Baker JG, Fischer PM, Hill SJ, Gardiner SM, Kellam B (2013) Synthesis and in vitro and in vivo characterization of highly β1-selective β-adrenoceptor partial agonists. J Med Chem 56(10):3852–3865
Buck JS, Ide WS (1935) Veratronitrile. Org Synth 15:85
Gawley RE (1988) The Beckmann reactions: rearrangements, elimination-additions, fragmentations, and rearrangement-cyclizations. In: Organic reactions, vol 35. Hoboken, NJ
Donaruma LG, Heldt WZ (1960) The Beckmann rearrangement. Org React 11:1–156
Tatsumi T (2001) Beckmann rearrangement. In: Sheldon RA, Bekkum H (eds). Wiley-VCH, Weinheim, pp 185–204
Kelly CB, Lambert KM, Mercadante MA, Ovian JM, Bailey WF, Leadbeater NE (2015) Access to nitriles from aldehydes mediated by an oxoammonium salt. Angew Chem Int Ed 54(14):4241–4245
Noh J-H, Kim J (2015) Aerobic oxidative conversion of aromatic aldehydes to nitriles using a nitroxyl/NO x catalyst system. J Org Chem 80(22):11624–11628
Wu Q, Luo Y, Lei A, You J (2016) Aerobic copper-promoted radical-type cleavage of coordinated cyanide anion: nitrogen transfer to aldehydes to form nitriles. J Am Chem Soc 138(9):2885–2888
Sharghi H, Sarvari MH (2002) A direct synthesis of nitriles and amides from aldehydes using dry or wet alumina in solvent free conditions. Tetrahedron 58(52):10323–10328
Erman MB, Snow JW, Williams MJ (2000) A new efficient method for the conversion of aldehydes into nitriles using ammonia and hydrogen peroxide. Tetrahedron Lett 41(35):6749–6752
Furukawa N, Fukumura M, Akasaka T, Yoshimura T, Oae S (1980) A convenient preparation of nitriles by reaction of free sulfimide with aldehydes. Tetrahedron Lett 21(8):761–762
Georg GI, Pfeifer SA (1985) A one-step transformation of aromatic aldehydes to nitriles, using S, S-dimethylsulfurdiimide as iminating agent. isolation of dithiatetrazocines as reaction intermediates. Tetrahedron Lett 26(33):2739–2742
Carmeli M, Shefer N, Rozen S (2006) From aldehydes to nitriles, a general and high yielding transformation using HOF·CH3CN complex. Tetrahedron Lett 47(50):8969–8972
Arote ND, Bhalerao DS, Akamanchi KG (2007) Direct oxidative conversion of aldehydes to nitriles using IBX in aqueous ammonia. Tetrahedron Lett 48(21):3651–3653
Telvekar VN, Patel KN, Kundaikar HS, Chaudhari HK (2008) A novel system for the synthesis of nitriles from aldehydes using aqueous ammonia and sodium dichloroiodate. Tetrahedron Lett 49(14):2213–2215
Sridhar M, Reddy MKK, Sairam VV et al (2012) Acetohydroxamic acid: a new reagent for efficient synthesis of nitriles directly from aldehydes using Bi(OTf)3 as the catalyst. Tetrahedron Lett 53(21):3421–3424
Nandi GC, Laali KK (2013) Schmidt reaction in ionic liquids: highly efficient and selective conversion of aromatic and heteroaromatic aldehydes to nitriles with [BMIM(SO3H)][OTf] as catalyst and [BMIM][PF6] as solvent. Tetrahedron Lett 54(17):2177–2179
Bose DS, Narsaiah AV (1998) Efficient one pot synthesis of nitriles from aldehydes in solid state using peroxymonosulfate on alumina. Tetrahedron Lett 39(36):2177–2179
Yamazaki S, Yamazaki Y (1990) A catalytic synthesis of nitriles from aldehydes and alcohols in the presence of aqueous ammonia by oxidation of NiSO4–K2S2O8. Chem Lett 19(4):571–574
Dornan LM, Cao Q, Flanagan JCA, Crawford JJ, Cook MJ, Muldoon MJ (2013) Copper/TEMPO catalysed synthesis of nitriles from aldehydes or alcohols using aqueous ammonia and with air as the oxidant. Chem Commun 49(54):6030–6032
Laulhé S, Gori SS, Nantz MH (2012) A chemoselective, one-pot transformation of aldehydes to nitriles. J Org Chem 77(20):9334–9337
Veisi H (2010) Direct oxidative conversion of alcohols, amines, aldehydes, and benzyl halides into the corresponding nitriles with trichloroisocyanuric acid in aqueous ammonia. Synthesis 15:2631–2635
Zhu C, Sun C, Wei Y (2010) Direct oxidative conversion of alcohols, aldehydes and amines into nitriles using hypervalent iodine(III) reagent. Synthesis 24:4235–4241
Arques A, Molina P, Soler A (1980) A new synthesis of nitriles from aldehydes. Synthesis 9:702–704
Capdevielle P, Lavigne A, Maumy M (1989) Simple and efficient copper-catalyzed one-pot conversion of aldehydes into nitriles. Synthesis 6:451–452
Lai G, Bhamare NK, Anderson WK (2001) A one-pot method for the efficient preparation of aromatic nitriles from aldehydes using ammonia, magnesium sulfate, and manganese dioxide. Synlett 2:230–231
Bandgar BP, Makone SS (2003) Organic reactions in water: highly rapid CAN mediated one-pot synthesis of nitriles from aldehydes under mild conditions. Synlett 2:262–264
Yamaguchi K, Fujiwara H, Ogasawara Y, Kotani M, Mizuno N (2007) A tungsten–tin mixed hydroxide as an efficient heterogeneous catalyst for dehydration of aldoximes to nitriles. Angew Chem Int Ed 46(21):3922–3925
Ishida T, Watanabe H, Takei T, Hamasaki A, Tokunaga M, Harut M (2012) Metal oxide-catalyzed ammoxidation of alcohols to nitriles and promotion effect of gold nanoparticles for one-pot amide synthesis. Appl Catal A 425–426:85–90
Oishi T, Yamaguchi K, Mizuno N (2009) Catalytic oxidative synthesis of nitriles directly from primary alcohols and ammonia. Angew Chem Int Ed 48(34):6286–6288
Iida S, Togo H (2007) Direct oxidative conversion of alcohols and amines to nitriles with molecular iodine and DIH in aq NH3. Tetrahedron 63(34):8274–8281
Iida S, Togo H (2007) Oxidative conversion of primary alcohols, and primary, secondary, and tertiary amines into the corresponding nitriles with 1,3-diiodo-5,5-dimethylhydantoin in aqueous NH3. Synlett 3:407–410
Reddy KR, Maheswari CU, Venkateshwar M, Prashanthi S, Kantam ML (2009) Catalytic oxidative conversion of alcohols, aldehydes and amines into nitriles using KI/I2–TBHP system. Tetrahedron Lett 50(18):2050–2053
Rokade BV, Malekar SK, Prabhu KR (2012) A novel oxidative transformation of alcohols to nitriles: an efficient utility of azides as a nitrogen source. Chem Commun 48(44):5506–5508
Yamaguchi K, Kobayashi H, Wang Y, Oishi T, Ogasawara Y, Mizuno N (2013) Green oxidative synthesis of primary amides from primary alcohols or aldehydes catalyzed by a cryptomelane-type manganese oxide-based octahedral molecular sieve, OMS-2. Catal Sci Technol 3(2):318–327
Tao C, Liu F, Zhu Y, Liu W, Cao Z (2013) Copper-catalyzed aerobic oxidative synthesis of aryl nitriles from benzylic alcohols and aqueous ammonia. Org Biomol Chem 11(20):3349–3354
Tan D-W, Xie J-B, Li Q, Li H-X, Li J-C, Li H-Y, Lang J-P (2014) Syntheses and structures of copper complexes of 3-(6-(1H-pyrazol-1-yl)pyridin-2-yl)pyrazol-1-ide and their excellent performance in the syntheses of nitriles and aldehydes. Dalton Trans 43(37):14061–14071
Xie J-B, Bao J-J, Li H-X, Tan D-W, Li H-Y, Lang J-P (2014) An efficient approach to the ammoxidation of alcohols to nitriles and the aerobic oxidation of alcohols to aldehydes in water using Cu(II)/pypzacac complexes as catalysts. RSC Adv 4(96):54007–54017
Dighe SU, Chowdhury D, Batra S (2014) Iron nitrate/TEMPO: a superior homogeneous catalyst for oxidation of primary alcohols to nitriles in air. Adv Synth Catal 356(18):3892–3896
Jagadeesh RV, Junge H, Beller M (2014) Green synthesis of nitriles using non-noble metal oxides-based nanocatalysts. Nat Commun 5:4128
Yin W, Wang C, Huang Y (2013) Highly practical synthesis of nitriles and heterocycles from alcohols under mild conditions by aerobic double dehydrogenative catalysis. Org Lett 15(8):1850–1853
Ghorbani-Vaghei R, Veisi H (2009) Poly(N, N′-dichloro-N-ethylbenzene-1,3-disulfonamide) and N,N,N′,N′-tetrachlorobenzene-1,3-disulfonamide as novel reagents for the synthesis of N-chloroamines. Nitriles and Aldehydes. Synthesis 6:945–950
Shimojo H, Moriyama K, Togo H (2013) Simple one-pot conversion of alcohols into nitriles. Synthesis 45:2155–2164
Vatèle J-M (2014) One-pot oxidative conversion of alcohols into nitriles by using a TEMPO/PhI(OAc)2/NH4OAc system. Synlett 25:1275–1278
McAllister GD, Wilfred CD, Taylor RJK (2002) Tandem oxidation processes: the direct conversion of activated alcohols into nitriles. Synlett 8:1291–1292
Chen F-E, Li Y-Y, Xu M, Jia H-Q (2002) Tetrabutylammonium peroxydisulfate in organic synthesis; XIII. A simple and highly efficient one-pot synthesis of nitriles by nickel-catalyzed oxidation of primary alcohols with tetrabutylammonium peroxydisulfate. Synthesis 13:1804–1806
Yadav DKT, Bhanage BM (2013) Copper-catalyzed synthesis of nitriles by aerobic oxidative reaction of alcohols and ammonium formate. Eur J Org Chem 23:5106–5110
Gu L, Jin C (2015) Copper-catalyzed aerobic oxidative cleavage of C–C bonds in epoxides leading to aryl nitriles and aryl aldehydes. Chem Commun 51:6572–6575
Ge J-J, Yao C-Z, Wang M-M, Zheng H-X, Kang Y-B, Li Y Transition-metal-free deacylative cleavage of unstrained C(sp 3)–C(sp 2) bonds: cyanide-free access to aryl and aliphatic nitriles from ketones and aldehydes. Org Lett 18(2): 228–231
Xu B, Jiang Q, Zhao A, Jia J, Liu Q, Luo W, Guo C (2015) Copper-catalyzed aerobic conversion of the C=O bond of ketones to a C≡N bond using ammonium salts as the nitrogen source. Chem Commun 51(56):11264–11267
Kende AS, Liu K (1995) The facile fragmentation of trifluoroacetyl groups to nitriles. Tetrahedron Lett 36(23):4035–4038
Kamijo S, Hoshikawa T, Inoue M (2010) Regio- and stereoselective acylation of saturated carbocycles via Norrish–Yang photocyclization. Tetrahedron Lett 51(5):872–874
Arora PK, Sayre LM (1991) Copper-ammonia mediated oxidation of carbonyl compounds. Tetrahedron Lett 32(8):1007–1010
Zhang X, Li WZ (2006) Acid-promoted ring opening of α-hydroxyl cyclobutanones: a novel and facile one-pot synthesis of nitrile derivatives. Synth Commun 36:249–254
Feng Q, Song Q (2014) Copper-catalyzed decarboxylative C≡N triple bond formation: direct synthesis of benzonitriles from phenylacetic acids under O2 atmosphere. Adv Synth Catal 356(8):1697–1702
Carter KN, Hulse JE III (1982) Extensions of the hydrazone and Beckmann rearrangements. J Org Chem 47(11):2208–2210
Ferris AF (1959) α-Oximino ketones. I. The, “normal” and “abnormal” beckmann rearrangements. J Org Chem 24(4):580–581
Kaim LE, Meyer C (1996) An unprecedented radical reaction of benzotriazole derivatives. A new efficient method for the generation of iminyl radicals. J Org Chem 61(5):1556–1557
Denton WI, Bishop RB, Caldwell HP, Chapman HD (1950) Production of aromatic nitriles. Ind Eng Chem 42(5):796–800
Toland WG (1962) The formation of nitriles by reaction of terminal methyl groups with sulfur and anhydrous ammonia. J Org Chem 27(3):869–871
Rapolu CSR, Panja KR (1993) Highly selective V–P–O/γ-Al2O3 catalysts in the ammoxidation of toluene to benzonitrile. J Chem Soc Chem Commun 14:1175–1176
Chary KVR, Kumar CP, Murli A, Tripathi A, Clearfield A (2004) Studies on catalytic functionality of V2O5/Nb2O5 catalysts. J Mol Catal Chem 216(1):139–146
Sanati M, Andersson A (1990) Ammoxtoation of toluene over TiO2(B)-supported vanadium oxide catalysts. J Mol Catal 59(2):233–255
Cavalli P, Cavani F, Manenti I, Trifirò F (1987) Ammoxidation of toluene to benzonitrile on vanadium-titanium oxides catalysts prepared by precipitation. The role of catalyst composition. Ind Eng Chem Res 26(4):639–647
Cavani F, Parrinello F, Trifirò F (1987) Synthesis of aromatic nitriles by vapour phase catalytic ammoxidation. J Mol Catal 43(1):117–125
Zheng Q, Huang C, Xie G, Xu C, Chen Y (1999) A direct synthesis of aromatic nitriles from methylaromatic compounds by ammoxidation on DC-108 catalyst. Synth Commun 29(13):2349–2353
Kumar CP, Reddy KR, Rao VV, Chary KVR (2002) Vapour phase ammoxidation of toluene over vanadium oxide supported on Nb2O5–TiO2. Green Chem 4(5):513–516
Belter RK (2011) High temperature vapor phase reactions of nitrogen trifluoride with benzylic substrates. J Fluor Chem 132(5):318–322
Zhou W, Zhang L, Jiao N (2009) Direct transformation of methyl arenes to aryl nitriles at room temperature. Angew Chem Int Ed 48(38):7094–7097
Diana GD, Cutcliffe D, Volkots DL, Mallamo JP, Bailey TR, Vescio N, Oglesby RC, Nitz TJ, Wetzel J, Giranda V, Pevear DC, Dutko FJ (1993) Antipicornavirus activity of tetrazole analogs related to disoxaril. J Med Chem 36(22):3240–3250
Guo S, Wan G, Sun S, Jiang Y, Yu J-T, Cheng J (2015) Iodine-catalyzed ammoxidation of methyl arenes. Chem Commun 51(24):5085–5088
Sasson R, Rozen S (2005) From azides to nitriles. A novel fast transformation made possible by Br F3. Org Lett 7(11):2177–2179
He J, Yamaguchi K, Mizuno N (2011) Aerobic oxidative transformation of primary azides to nitriles by ruthenium hydroxide catalyst. J Org Chem 76(11):4606–4610
Zhou W, Xu J, Zhang L, Jiao N (2010) An efficient transformation from benzyl or allyl halides to aryl and alkenyl nitriles. Org Lett 12(12):2888–2891
Tsuchiya D, Kawagoe Y, Moriyama K, Togo H (2013) Direct oxidative conversion of methylarenes into aromatic nitriles. Org Lett 15(16):4194–4197
Kawagoe Y, Moriyama K, Togo H (2014) One-pot transformation of methylarenes into aromatic nitriles with inorganic metal-free reagents. Eur J Org Chem 2014(19):4115–4122
Okamoto K, Eger BT, Nishuno T, Kondo S, Pai EF, Nishino T (2003) An extremely potent inhibitor of xanthine oxidoreductase. J Biol Chem 278(3):1848–1855
Wang Y, Yamaguchi K, Mizuno N (2012) Manganese oxide promoted liquid-phase aerobic oxidative amidation of methylarenes to monoamides using ammonia surrogates. Angew Chem Int Ed 51(29):7250–7253
Shu Z, Ye Y, Deng Y, Zhang Y, Wang J (2013) Palladium(II)-catalyzed direct conversion of methyl arenes into aromatic nitriles. Angew Chem Int Ed 52(40):10573–10576
Kim HS, Kim SH, Kim JN (2009) Highly efficient Pd-catalyzed synthesis of nitriles from aldoximes. Tetrahedron Lett 50(15):1717–1719
Fleming FF, Yao L, Ravikumar PC, Funk L, Shook BC (2010) Nitrile-containing pharmaceuticals: efficacious roles of the nitrile pharmacophore. J Med Chem 53(22):7902–7917
Liu J, Zheng H-X, Yao C-Z, Sun B-F, Kang Y-B (2016) Pharmaceutical-oriented selective synthesis of mononitriles and dinitriles directly from methyl(hetero)arenes: access to chiral nitriles and citalopram. J Am Chem Soc 138(10):3294–3297
Zong H, Huang H, Liu J, Bian G, Song L (2012) Added-metal-free catalytic nucleophilic addition of grignard reagents to ketones. J Org Chem 77(10):4645–4652
Chen F, Huang X, Cui Y, Jiao N (2013) Direct transformation of methyl imines to α-iminonitriles under mild and transition-metal-free conditions. Chem Eur J 19(34):11199–11202
Wu D, Zhang J, Cui J, Zhang W, Liu Y (2014) AgNO2-mediated direct nitration of the quinoxaline tertiary benzylic C–H bond and direct conversion of 2-methyl quinoxalines into related nitriles. Chem Commun 50:10857–10860
Milberger EC, Wong EKT (1983) European Patent Applications, 82620, 29 Jun 1983
Reed SA, Mazzotti AR, White MC (2009) A catalytic, Brønsted base strategy for intermolecular allylic C–H amination. J Am Chem Soc 131(33):11701–11706
Liu G, Yin G, Wu L (2008) Palladium-catalyzed intermolecular aerobic oxidative amination of terminal alkenes: efficient synthesis of linear allylamine derivatives. Angew Chem Int Ed 47(25):4733–4736
Shimizu Y, Obora Y, Ishii Y (2010) Intermolecular aerobic oxidative allylic amination of simple alkenes with diarylamines catalyzed by the Pd(OCOCF3)2/NPMoV/O2 system. Org Lett 12(6):1372–1374
Qin C, Jiao N (2010) Iron-facilitated direct oxidative C–H transformation of allylarenes or alkenes to alkenyl nitriles. J Am Chem Soc 132(45):15893–15895
Simmons EM, Hartwig JF (2012) On the interpretation of deuterium kinetic isotope effects in C–H bond functionalizations by transition-metal complexes. Angew Chem Int Ed 51(13):3066–3072
Zhou W, Xu J, Zhang L, Jiao N (2011) An efficient approach to alkenyl nitriles from allyl esters. Synlett 7:887–890
Grubbs RH, Miller SJ, Fu GC (1995) Ring-closing metathesis and related processes in organic synthesis. Acc Chem Res 28(11):446–452
Chen YL (1965) Carbon-carbon doubie bond cleavage by photoaddition of N-nitrosodialkylamine to olefins. J Am Chem Soc 87(20):4642–4643
Wang T, Jiao N (2013) TEMPO-catalyzed aerobic oxygenation and nitrogenation of olefins via C=C double-bond cleavage. J Am Chem Soc 135(32):11692–11695
Yokoyama R, Matsumoto S, Nomura S, Higaki T, Yokoyama T, Kiyooka S (2009) Enantioselective construction of nitrogen-substituted quaternary carbon centers adjacent to the carbonyl group in the cyclohexane ring: first asymmetric synthesis of anesthetic (S)-ketamine with high selectivity. Tetrahedron 65(27):5181–5191
Sun X, Li X, Song S, Zhu Y, Liang Y-F, Jiao N (2015) Mn-catalyzed highly efficient aerobic oxidative hydroxyazidation of olefins: a direct approach to azido alcohols. J Am Chem Soc 137(18):6059–6066
Zong X, Zheng Q-Z, Jiao N (2014) NBS mediated nitriles synthesis through C=C double bond cleavage. Org Biomol Chem 12:1198–1202
Dornan LM, Cao Q, Flanagan JCA, Crawford JJ, Cook MJ, Muldoon MJ (2013) Copper/TEMPO catalysed synthesis of nitriles from aldehydes or alcohols using aqueous ammonia and with air as the oxidant. Chem Commun 49:6030–6032
Chiba S, Zhang L, Ang GY, Hui BW (2010) Generation of iminyl copper species from α-azido carbonyl compounds and their catalytic C–C bond cleavage under an oxygen atmosphere. Org Lett 12(9):2052–2055
Xu S, Cai T, Yun Z (2016) Cobalt-containing mesoporous ZSM-5 zeolite catalyzed C=C bond cleavage of alkenes to form nitriles. Synlett 27(2):221–224
Xu J-H, Jiang Q, Guo C-C (2013) Phenyliodonium diacetate mediated direct synthesis of benzonitriles from styrenes through oxidative cleavage of C=C bonds. J Org Chem 78(23):11881–11886
Emmanuvel L, Shaikh TMA, Sudalai A (2005) NaIO4/LiBr-mediated diastereoselective dihydroxylation of olefins: a catalytic approach to the Prevost–Woodward reaction. Org Lett 7(22):5071–5074
Liu Q, Fang B, Bai X, Liu Y, Wu Y, Xu G, Guo C (2016) Direct synthesis of nitriles from cleavage of C=C double bond with nitrite as the nitrogen source and oxidant. Tetrahedron Lett 57(24):2620–2623
Amblard F, Cho JH, Schinazi RF (2009) Cu(I)-catalyzed Huisgen azide–alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry. Chem Rev 109(9):4207–4220
Haines AH (1985) Methods for the oxidation of organic compounds. Alkanes, alkenes, alkynes, and arenes. Academic Press, New York
Takaya H, Noyori R (1991) In: Trost BM, Fleming I (eds) Comprehensive organic synthesis. Pergamon, Oxford
Shen T, Wang T, Qin C, Jiao N (2013) Silver-catalyzed nitrogenation of alkynes: a direct approach to nitriles through C≡C bond cleavage. Angew Chem Int Ed 52(26):6677–6680
Kadaba PK (1990) Triazolines XX. Vinyl azides as dipolarophiles in 1,3-dipolar cycloadditions: intermolecular cycloaddition of hydrazoic acid and α-styryl azide to give a tetrazole. Synlett 6:349–351
Okamoto N, Ishikura M, Yanada R (2013) Cleavage of carbon≡carbon triple bond: direct transformation of alkynes to nitriles. Org Lett 15(11):2571–2573
Jung N, Bräse S (2012) Vinyl and alkynyl azides: well-known intermediates in the focus of modern synthetic methods. Angew Chem Int Ed 51(49):12169–12171
Banert K, Fotsing JR, Hagedorn M, Reisenauer HP, Maier G (2008) Photolysis of open-chain 1,2-diazidoalkenes: generation of 2-azido-2H-azirines, formyl cyanide, and formyl isocyanide. Tetrahedron 64(24):5645–5648
Dutta U, Lupton DW, Maiti D (2016) Aryl nitriles from alkynes using tert-butyl nitrite: metal-free approach to C≡C bond cleavage. Org Lett 18(4):860–863
Sherwood AG, Gunning HE (1963) Reactions of unsaturated free radicals with nitric oxide. Radical-induced scission of carbon–carbon triple bonds. J Am Chem Soc 85(21):3506–3508
Huang X, Li X, Jiao N (2015) Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative nincorporation. Chem Sci 6:6355–6360
Liang Y, Zhou H, Yu Z-X (2009) Why is copper(I) complex more competent than dirhodium(II) complex in catalytic asymmetric O–H insertion reactions? A computational study of the metal carbenoid O–H insertion into water. J Am Chem Soc 131(49):17783–17785
Banert K, Arnold R, Hagedorn M, Thoss P, Auer AA (2012) 1-Azido-1-alkynes: synthesis and spectroscopic characterization of azidoacetylene. Angew Chem Int Ed 51(13):7515–7518
Lee E, Kamlet AS, Powers DC, Neumann CN, Boursalian GB, Furuya T, Choi DC, Hooker JM, Ritter T (2011) A fluoride-derived electrophilic late-stage fluorination reagent for PET imaging. Science 334(6056):639–642
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2017 Springer Nature Singapore Pte Ltd.
About this chapter
Cite this chapter
Wang, T., Jiao, N. (2017). Nitrogenation Strategy for the Synthesis of Nitriles. In: Jiao, N. (eds) Nitrogenation Strategy for the Synthesis of N-containing Compounds. Springer, Singapore. https://doi.org/10.1007/978-981-10-2813-7_4
Download citation
DOI: https://doi.org/10.1007/978-981-10-2813-7_4
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-10-2811-3
Online ISBN: 978-981-10-2813-7
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)