Abstract
Recent progress in the area of hypervalent iodine-mediated and catalyzed amination reaction of hydrocarbons is reviewed. These reactions comprise processes under both intra and intermolecular control and include the functionalization of aromatic C–H bonds as well as conversion of sp-, sp2-, and sp3-hybridized carbon atoms. These developments demonstrate that hypervalent iodine(III) methodology has reached a high level in amination chemistry. The individual reactions are discussed with a focus on mechanistic details and emphasis is made to the underlying hypervalent iodine reagents, for which structural information is available.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Zhdankin VV (2014) Hypervalent iodine chemistry. Wiley, Chichester
Koser GF (2003) In: Wirth T (ed) Hypervalent iodine chemistry. Modern developments in organic synthesis, Topic curr chem 224. Springer, Berlin/Heidelberg, pp 138–172
Samanta R, Matcha K, Antonchick AP (2013) Eur J Org Chem 5769
Narayan R, Manna S, Antonchick AP (2015) Synlett 26:1785
Cho SH, Yoon J, Chang S (2011) J Am Chem Soc 133:5996
Antonchick AP, Samanta R, Kulikov K, Lategahn J (2011) Angew Chem Int Ed 50:8605
Ban X, Pan Y, Lin Y, Wang S, Du Y, Zhao K (2012) Org Biomol Chem 10:3606
Du Y, Liu R, Linn G, Zhao K (2006) Org Lett 8:5919
Fra L, Millán E, Souto JA, Muñiz K (2014) Angew Chem Int Ed 53:7349
Huang J, He Y, Wang Y, Zhu Q (2012) Chem Eur J 18:13964
Alla SK, Kumar RK, Sadhu P, Punniyamurthy T (2013) Org Lett 15:1334
Chi Y, Zhang W-X, Xi Z (2014) Org Lett 16:6274
Maiti S, Mal P (2015) Adv Synth Catal 357:1416
He Y, Huang J, Liang D, Liu L, Zhu Q (2013) Chem Commun 49:7352
Liang D, He Y, Liu L, Zhu Q (2013) Org Lett 15:3476
Wang H, Wang Y, Peng C, Zhang J, Zhu Q (2010) J Am Chem Soc 132:13217
Chu J-H, Hsu W-T, Wu Y-H, Chaing M-F, Hsu N-H, Huang H-P, Wu J (2014) J Org Chem 79:11395
Dohi T, Maruyama A, Minamitsuji Y, Takenaga T, Kita Y (2007) Chem Commun 43:1224
Dohi T, Takenaga N, Fukushima K-I, Uchiyama T, Kato D, Shiro M, Fujioka H, Kita Y (2010) Chem Commun 46:7697
Kim HJ, Kim J, Cho H, Chang S (2011) J Am Chem Soc 133:16382
Kantak AA, Potavathri S, Barham RA, Romano KM, DeBoef B (2011) J Am Chem Soc 133:19960
Moriyama K, Ishida K, Togo H (2012) Org Lett 14:946
Itoh N, Sakamoto T, Miyazawa E, Kikugawa Y (2002) J Org Chem 67:7424
Samantha R, Lategahn I, Antonchick AP (2012) Chem Commun 48:3194
Souto JA, Martínez C, Velilla I, Muñiz K (2013) Angew Chem Int Ed 52:1324
Samantha R, Bauer JO, Strohmann C, Antonchick AP (2012) Org Lett 14:5518
Manna S, Serebrennikova PO, Utepova IA, Antonchick AP (2015) Org Lett 17:4588
Ivanov AS, Popov IA, Boldyrev AI, Zhdankin VV (2014) Angew Chem Int Ed 53:9617
Macikenas D, Skrypczak-Jankun E, Protasiewicz JD (1999) J Am Chem Soc 121:7164
Meprathu BV, Protasiewicz JD (2010) Tetrahedron 66:5768
Meprathu BV, Protasiewicz JD (2003) Arkivoc VI:83
Yoshimura A, Nemykin VN, Zhdankin VV (2011) Chem Eur J 17:10538
Müller P (1997) Adv Catal Processes 2:113
Padwa A, Stengel T (2002) Org Lett 4:2137
Moriarty RM, Tyagi S (2010) Org Lett 12:364
Liu Z-G, Cheng H, Ge M-J, Xu L, Wang F-P (2013) Tetrahedron 69:5431
Mei R-H, Liu Z-G, Cheng H, Xu L, Wang F-P (2013) Org Lett 15:2206
Li J, Liang J-L, Chan PWH, Che C-M (2005) Org Lett 7:5801
Li J, Liang J-L, Chan PWH, Che C-M (2004) Tetrahedron Lett 45:2685
Richardson RD, Desaize M, Wirth T (2007) Chem Eur J 13:6745
Ochiai M, Kaneaki T, Tada N, Miyamoto K, Chuman H, Shiro M, Hayashi S, Nakanishi W (2007) J Am Chem Soc 129:12938
Ochiai M, Miyamoto K, Kaneaki T, Hayashi S, Nakanishi W (2011) Science 332:448
Muñiz K (2014) In: Molander G, Knochel P (eds) Comprehensive organic synthesis II, vol 7. Elsevier, Oxford, 411 p
Romero M, Wöste TH, Muñiz K (2014) Chem Asian J 9:950
Singh FV, Wirth T (2014) Chem Asian J 9:950
Liang H, Ciufolini MA (2011) Angew Chem Int Ed 50:11849
Correa A, Tellitu I, Domínguez E, SanMartin R (2006) J Org Chem 71:8316
Tellitu I, Domínguez E (2011) Trends Heterocycl Chem 15:23
Wardrop DJ, Bowen EG (2011) Org Lett 13:2376
Bowen EG, Wardrop DJ (2010) Org Lett 12:5330
Cochran BM, Michael FE (2008) Org Lett 10:5039
Lovick HM, Michael FE (2010) J Am Chem Soc 132:1249
Chen H, Kaga A, Chiba S (2014) Org Lett 16:6136
Farid U, Wirth T (2012) Angew Chem Int Ed 51:3462
Kong W, Beige P, de Haro T, Nevado C (2013) Angew Chem Int Ed 52:2469
Wang Q, Zhong W, Wei X, Ning M, Mang X, Li Z (2012) Org Biomol Chem 10:8566
Liu G-Q, Li Y-M (2014) J Org Chem 79:10094
Moriarty RM, Khosrowshahi JS (1986) Tetrahedron Lett 27:2809
Magnus P, Lacour J, Evans PA, Roe MB, Hulme C (1996) J Am Chem Soc 118:3406
Magnus P, Lacour J (1992) J Am Chem Soc 114:767
Magnus P, Lacour J (1992) J Am Chem Soc 114:3993
Magnus P, Roe MB, Hulme C (1995) Chem Commun 263
Martínez C, Muñiz K (2013) J Org Chem 78:2168
Yang H-T, Lu X-W, Xing M-L, Sun X-Q, Miao C-B (2014) Org Lett 16:5882
Röben C, Souto JA, González Y, Lishchynskyi A, Muñiz K (2011) Angew Chem Int Ed 50:9478
Souto JA, González Y, Iglesias A, Zian D, Lishchynskyi A, Muñiz K (2012) Chem Asian J 7:1103
Kong A, Blakey SB (2012) Synthesis 44:1190
Röben C, Souto JA, Escudero-Adán E, Muñiz K (2013) Org Lett 15:1008
Hong KB, Johnston JN (2014) Org Lett 16:3804
Danneman MW, Hong KB, Johnston JN (2015) Org Lett 17:2558
Danneman MW, Hong KB, Johnston JN (2015) Org Lett 17:3806
Lishchynskyi A, Muñiz K (2012) Chem Eur J 18:2213
Purkait N, Okumura S, Souto JA, Muñiz K (2014) Org Lett 16:4750
Yoshimura A, Koski SR, Fuchs JM, Saito A, Nemykin VN, Zhdankin VV (2015) Chem Eur J 21:5328
Mao L, Li Y, Xiong T, Sun K, Zhang Q (2013) J Org Chem 78:733
Souto JA, Zian D, Muñiz K (2012) J Am Chem Soc 134:7242
Kiyokawa K, Yahata S, Kojima T, Minakata S (2014) Org Lett 16:4646
Souto J, Becker P, Iglesias A, Muñiz K (2012) J Am Chem Soc 134:15505
Nagashima K, Sakamoto T, Kikugawa Y (2007) Heterocycles 74:273
Hernández R, Rivera A, Salazar JA, Suárez E (1980) Chem Commun 958
Betancor C, Concepción JI, Hernández R, Salazar JA, Suárez E (1983) J Org Chem 48:4430
De Armas P, Carrau R, Concepción JI, Francisco CG, Hernández R, Suárez E (1985) Tetrahedron Lett 26:2493
Carrau R, Hernández R, Suárez E, Betancor C (1987) Perkin Trans 1 937
De Armas P, Francisco CG, Hernández R, Salazar JA, Suárez E (1988) Perkin Trans 1 3255
Fan R, Pu D, Wen F, Wu J (2007) J Org Chem 72:8994
Kim YR, Cho S, Lee PH (2014) Org Lett 16:3098
Martínez C, Muñiz K (2015) Angew Chem Int Ed 54:8287
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Muñiz, K. (2015). Aminations with Hypervalent Iodine. In: Wirth, T. (eds) Hypervalent Iodine Chemistry. Topics in Current Chemistry, vol 373. Springer, Cham. https://doi.org/10.1007/128_2015_663
Download citation
DOI: https://doi.org/10.1007/128_2015_663
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-33731-9
Online ISBN: 978-3-319-33733-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)