Abstract
Cross-dehydrogenative-coupling (CDC) reactions involving C–H bond activation are powerful tools for C–C bond formation and are highly significant from the perspective of atom economy. A variety of carbon–carbon bond-forming reactions utilizing various coupling partners are known today. Iron-catalyzed organic syntheses have attracted considerable attention because iron is an abundant, inexpensive, and environmentally benign metal. This chapter summarizes the development of iron-catalyzed CDC reactions, the reaction mechanism, and the role of the Fe species in the catalytic cycle in the period from 2007 to 2014.
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- Å:
-
Ångström
- acac:
-
Acetylacetone
- Boc:
-
tert-Butoxycarbonyl
- cat.:
-
Catalyst
- CDC:
-
Cross-dehydrogenative coupling
- Cp:
-
Cyclopentadienyl
- dbm:
-
Dibenzoylmethane
- DCE:
-
1,2-Dichloroethane
- DDQ:
-
2,3-Dichloro-5,6-dicyano-p-benzoquinone
- dr :
-
Diastereomeric ratio
- equiv.:
-
Equivalent(s)
- Et:
-
Ethyl
- h:
-
Hour(s)
- Me:
-
Methyl
- min:
-
Minute(s)
- MS:
-
Molecular sieves
- Pr:
-
n-Propyl
- Ph:
-
Phenyl
- pin:
-
Pinacol
- rt:
-
Room temperature
- Bu:
-
tert-Butyl
- SET:
-
Single-electron transfer
- TEMPO:
-
2,2,6,6-Tetramethylpiperidine-1-oxyl
- TfO:
-
Trifluoromethanesulfonate
- TON:
-
Turnover number
- Ts:
-
4-Toluensulfonyl
References
Diederich F, Stang PJ (eds) (2004) Metal-catalyzed cross-coupling reactions. Wiley, Weinheim
Seechurn CCCJ, Kitching MO, Colacot TJ, Snieckus V (2012) Angew Chem Int Ed 51:5062
Beletskaya IP, Cheprakov AV (2009) In: Oestreich M (ed) The Mizoroki-Heck reaction. Wiley, Chichester
Torborg C, Beller M (2009) Adv Synth Catal 351:3027
Beller M (2011) Chem Soc Rev 40:4891
Li C-J (2009) Acc Chem Res 42:335, and the references therein
Guo X, Li Z, Li C-J (2010) Prog Chem 22:1434
Li Z, Cao L, Li C-J (2007) Angew Chem Int Ed 46:6505
Zhang Y, Li C-J (2007) Eur J Org Chem 4654
Huyser ES, Munson LR (1965) J Org Chem 30:1436
Li Z, Yu R, Li H (2008) Angew Chem Int Ed 47:7497
Mbuvi HM, Woo LK (2008) Organometallics 27:637
Li Y, Huang J-S, Zhou Z-Y, Che C-M, You X-Z (2002) J Am Chem Soc 124:13185
Li H, He Z, Guo X, Li W, Zhao X, Li Z (2009) Org Lett 11:4176
Zeng T, Song G, Moores A, Li C-J (2010) Synlett 13:2002
Hudson R, Ishikawa S, Li C-J, Moores A (2013) Synlett 24:1637
Li Z, Li C-J (2005) J Am Chem Soc 127:3672
Baslè O, Li C-J (2009) Chem Commun 4124
Evans DA, Seidel D, Rueping M, Lam HW, Shaw JT, Downey CW (2003) J Am Chem Soc 125:12692
Shen Y, Li M, Wang S, Zhan T, Tan Z, Guo C-C (2009) Chem Commun 953
Richter H, Mancheño OG (2010) Eur J Org Chem 4460
Xu YC, Lebeau E, Gillard JW, Attardo G (1993) Tetrahedron Lett 34:3841
Lou S-J, Xu D-Q, Shen D-F, Wang Y-F, Liu Y-K, Xu Z-Y (2012) Chem Commun 48:11993
Qian B, Guo S, Shao J, Zhu Q, Yang L, Xia C, Huang H-M (2010) J Am Chem Soc 132:3650
Rueping M, Tolstoluzhsky N (2011) Org Lett 13:1095
Komai H, Yoshino T, Matsunaga S, Kanai M (2011) Org Lett 13:1706
Song G-Y, Su Y, Gong X, Han K-L, Li X-W (2011) Org Lett 13:1968
Qian B, Xie P, Xie Y-J, Huang H-M (2011) Org Lett 13:2580
Tsuchimoto T, Ozawa Y, Negoro R, Shirakawa E, Kawakami Y (2004) Angew Chem Int Ed 43:4231
Ghobrial M, Harhammer K, Mihovilovic MD, Schnürch M (2010) Chem Commun 46:8836
Shirakawa E, Uchiyama N, Hayashi T (2011) J Org Chem 76:25
Wei Y, Ding H-Q, Lin S-X, Liang F-S (2011) Org Lett 13:1674
Minisci F (1973) Synthesis 1
Minisci F, Porta O (1974) In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol. 16. Academic, New York, p 123
Minisci F (1976) Top Curr Chem 62:1
Minisci F, Porta O (1980) Chim Ind 62:769
Minisci F (1984) In: Graziani M (ed) Fundamental research in homogenous catalysis, vol 4. Plenum, New York, p 173
Minisci F (1986) In: Viehe HG (ed) Substituent effects in radical chemistry. Reidel, Boston, p 391
Minisci F, Vismara E (1987) In: Chizhov O (ed) Organic synthesis: modern trends. Blackwell Scientific, Oxford, p 229
Minisci F, Fontana F, Vismara E (1989) Heterocycles 28:489
Minisci F, Fontana F, Vismara EJ (1990) Heterocycl Chem 27:79
Li Y-Z, Li B-J, Lu X-Y, Lin S, Shi Z-J (2009) Angew Chem Int Ed 48:3817
Song C-X, Cai G-X, Farrell TR, Jiang Z-P, Li H, Gan L-B, Shi Z-J (2009) Chem Commun 6002
Guo X, Pan S, Liu J, Li Z (2009) J Org Chem 74:8848
Ono N (ed) (2001) The nitro group in organic synthesis. Wiley, New York
Guo X, Yu R, Li H, Li Z (2009) J Am Chem Soc 131:17387
Yoshikai N, Matsumoto A, Norinder J, Nakamura E (2009) Angew Chem Int Ed 48:2925
Norinder J, Matsumoto A, Yoshikai N, Nakamura E (2008) J Am Chem Soc 130:5858
Liu H, Cao L, Sun J, Fosseyab JS, Deng W (2012) Chem Commun 48:2674
Wang Z, Mo H, Cheng D, Bao W (2012) Org Biomol Chem 10:4249
Pan S, Liu J, Li H, Wang Z, Guo X, Li Z (2010) Org Lett 12:1932
Liu X, Chen Y, Li K, Wang D, Chen B (2012) Chin J Chem 30:2285
Li Y, Cao L, Luo X, Deng W (2012) Chin J Chem 30:2834
Sun M, Zhang T, Bao W (2013) J Org Chem 78:8155
Yang J, Wang Z, Pan F, Li Y, Bao W (2010) Org Biomol Chem 8:2975
Parnes R, Kshirsagar UA, Werbeloff A, Regev C, Pappo D (2012) Org Lett 14:3324
Kshirsagar UA, Parnes R, Goldshtein H, Ofir R, Zarivach R, Pappo D (2013) Chem Eur J 19:13575
Volla CMR, Vogel P (2009) Org Lett 11:1701
Horner L, Junkermann H (1955) Ann Chem Justus Liebigs 591:53
Horner L, Kirmse W (1955) Ann Chem Justus Liebigs 597:48
Li P, Zhang Y, Wang L (2009) Chem Eur J 15:2045
Liu P, Wang Z, Lin J, Hu X (2012) Eur J Org Chem 1583
Chandrasekharam M, Chiranjeevi B, Gupta KSV, Sridhar B (2011) J Org Chem 76:10229
Griffin BW (1978) Arch Biochem Biophys 190:850
Chiranjeevi B, Koyyada G, Prabusreenivasan S, Kumar V, Sujitha P, Kumar CG, Sridhar B, Shaike S, Chandrasekharam M (2013) RSC Adv 3:16475
Qian B, Zhang G, Ding Y, Huang H (2013) Chem Commun 49:9839
Grau M, Britovsek GJP (2015) High-valent iron in biomimetic alkane oxidation catalysis. Top Organomet Chem. doi:10.1007/3418_2015_100
Chang S, Scharre E, Brookhart M (1998) J Mol Catal A 130:107
Rommel S, Hettmanczyk L, Klein JEMN, Plietker B (2014) Chem Asian J 9:2140
Teo AKL, Fan WY (2014) Chem Commun 50:7191
Fukumoto K, Kasa M, Nakazawa H (2014) Accepted in Inorg Chim Acta. doi:10.1016/j.ica.2015.02.019
Fukumoto K, Kasa M, Oya T, Itazaki M, Nakazawa H (2011) Organometallics 30:3461
Ito M, Itazaki M, Nakazawa H (2014) J Am Chem Soc 136:6183
Marciniec B, Walkowiak J (2008) Chem Commun 2695
Soraru GD, Dallabona N, Gervais C, Babonneau F (1999) Chem Mater 11:910
Fujinami T, Mehta MA, Sugie K, Mori K (2000) Electrochim Acta 45:1181
Wang Q, Fu L, Hu X, Zhang Z, Xie Z (2006) J Appl Polym Sci 99:719
Peña-Alonso R, Mariotto G, Gervais C, Babonneau F, Soraru GD (2007) Chem Mater 19:5694
Acknowledgment
We would like to show our respect for the great efforts of all authors, whose names were listed in the references. We wish to thank Dr. Yuji Suzaki for the reference collection.
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Itazaki, M., Nakazawa, H. (2015). Iron-Catalyzed Cross-Dehydrogenative-Coupling Reactions. In: Bauer, E. (eds) Iron Catalysis II. Topics in Organometallic Chemistry, vol 50. Springer, Cham. https://doi.org/10.1007/3418_2015_105
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DOI: https://doi.org/10.1007/3418_2015_105
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