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DOI: 10.1055/s-0034-1378373
Recent Advances in Electrophilic Amination Reactions
Publication History
Received: 26 March 2014
Accepted after revision: 09 June 2014
Publication Date:
15 July 2014 (online)
Abstract
Electrophilic nitrogen sources are an increasingly popular class of reagents for the formation of C–N bonds. Recently, a significant number of useful methodologies have been reported, in particular, examples using transition-metal catalysis. This review summarizes the latest developments in this field, with a focus on very recent advances.
1 Introduction
2 Reactions with Stoichiometric Organometallic Reagents
2.1 Organoboron Nucleophiles
2.2 Zirconium Derivatives
2.3 Silicon Derivatives
2.4 Grignard Reagents
2.5 Organozinc Reagents
3 Catalytic Organometallic Species
3.1 C–H Activation Reactions
3.2 Heterocycle Synthesis via Addition/Amination Sequences
3.3 Narasaka–Heck (or Amino-Heck) Reactions
4 Enolates as Nucleophiles
5 Conclusion
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References
- 1a Surry DS, Buchwald SL. Chem. Sci. 2011; 2: 27
- 1b Hartwig JF. Acc. Chem. Res. 2008; 41: 1534
- 2 Qiao JX, Lam PY. S. Synthesis 2011; 829
- 4a Brown HC, Hedkamp WR, Breuer E, Murphy WS. J. Am. Chem. Soc. 1964; 86: 3565
- 4b Brown HC, Kim K.-W, Srebnik M, Bakthan S. Tetrahedron 1987; 43: 4071
- 4c Rangaishenvi MV, Singaram B, Brown HC. J. Org. Chem. 1991; 56: 3286
- 5 Matsuda N, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2012; 51: 3642
- 6 Rucker RP, Whittaker AM, Dang H, Lalic G. Angew. Chem. Int. Ed. 2012; 51: 3953
- 7 Rucker RP, Whittaker AM, Dang H, Lalic G. J. Am. Chem. Soc. 2012; 134: 6571
- 8 Matsuda N, Hirano K, Satoh T, Miura M. J. Am. Chem. Soc. 2013; 135: 4934
- 9 Sakae R, Matsuda N, Hirano K, Satoh T, Miura M. Org Lett. 2014; 16: 1228
- 10 Xiao Q, Tian L, Tan R, Xia Y, Qiu D, Zhang Y, Wang J. Org. Lett. 2012; 14: 4230
- 11 Mlynarski NL, Karns AS, Morken JP. J. Am. Chem. Soc. 2012; 134: 16449
- 12 Zhu C, Li G, Ess DH, Falck JR, Kürti L. J. Am. Chem. Soc. 2012; 134: 18253
- 13 Pronin SV, Greg Tabor M, Jansen DJ, Shenvi RA. J. Am. Chem. Soc. 2012; 134: 2012
- 14 Yan X, Chen C, Zhou Y, Xi C. Org. Lett. 2012; 14: 4750
- 15 Liu H, Yan X, Chen C, Liu Q, Xi C. Chem. Commun. 2013; 49: 5513
- 16 Miki Y, Hirano K, Satoh T, Miura M. Org. Lett. 2013; 15: 172
- 17 Tsutsui H, Hayashi Y, Narasaka K. Chem. Lett. 1997; 26: 317
- 18 Campbell MJ, Johnson JS. Org. Lett. 2007; 9: 1521
- 19 Bermann AM, Johnson JS. Synlett 2005; 1799
- 20 Barker TJ, Jarvo ER. Angew. Chem. Int. Ed. 2011; 50: 8325
- 21 Mizutani Y, Tanimoto H, Morimoto T, Nishiyama Y, Kakiuchi K. Tetrahedron Lett. 2012; 53: 5903
- 22a Berman AM, Johnson JS. J. Am. Chem. Soc. 2004; 126: 5680
- 22b Berman AM, Johnson JS. J. Org. Chem. 2005; 70: 364
- 22c Berman AM, Johnson JS. Synlett 2005; 1799
- 22d Berman AM, Johnson JS. J. Org. Chem. 2006; 71: 219
- 23 Barker TJ, Jarvo ER. J. Am. Chem. Soc. 2009; 131: 15598
- 24a Fillon H, Gosmini C, Perichon J. J. Am. Chem. Soc. 2003; 125: 3867
- 24b Kazmierski I, Gosmini C, Paris J.-M, Perichon J. Tetrahedron Lett. 2003; 44: 6417
- 24c Gosmini C, Amatore M, Claudel S, Perichon J. Synlett 2005; 2171
- 25 Qian X, Yu Z, Auffrant A, Gosmini C. Chem. Eur. J. 2013; 19: 6225
- 26a Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236
- 26b Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
- 26c Wencel-Delord J, Dröge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
- 26d Du Bois J. Org. Process Res. Dev. 2011; 15: 758
- 26e Stokes BJ, Driver TG. Eur. J. Org. Chem. 2011; 4071
- 26f Collet F, Dodd RH, Dauban P. Chem. Commun. 2009; 5061
- 27a Kawano T, Hirano K, Satoh T, Miura M. J. Am. Chem. Soc. 2010; 132: 3676
- 27b Guimond N, Gouliaras C, Fagnou K. J. Am. Chem. Soc. 2010; 132: 6908
- 27c Wasa M, Yu J.-Q. J. Am. Chem. Soc. 2008; 130: 14058
- 27d Tan Y, Hartwig JF. J. Am. Chem. Soc. 2010; 132: 3676
- 28 Ng K.-H, Zhou Z, Yu W.-Y. Org Lett. 2012; 14: 272
- 29 Grohmann C, Wang H, Glorius F. Org. Lett. 2012; 14: 656
- 30 Grohmann C, Wang H, Glorius F. Org. Lett. 2013; 15: 3014
- 31 Ng K.-H, Zhou Z, Yu W.-Y. Chem. Commun. 2013; 49: 7031
- 32 Ryu J, Shin K, Park SH, Kim JY, Chang S. Angew. Chem. Int. Ed. 2012; 51: 9904
- 33 Tang R.-J, Luo C.-P, Yang L, Li C.-J. Adv. Synth. Catal. 2013; 355: 869
- 34 Sun K, Li Y, Xiong T, Zhang J, Zhang Q. J. Am. Chem. Soc. 2011; 133: 1694
- 35 Yotphan S, Beukeaw D, Reutrakul V. Tetrahedron 2013; 69: 6627
- 36 Shang M, Zeng S.-H, Sun S.-Z, Dai H.-X, Yu J.-Q. Org. Lett. 2013; 15: 5286
- 37 Yoo E.-U, Ma S, Mei T.-S, Chan KS. L, Yu J.-Q. J. Am. Chem. Soc. 2011; 133: 7652
- 38a Stuart DR, Bertrand-Laperle M, Burgess KM. N, Fagnou K. J. Am. Chem. Soc. 2008; 130: 16474
- 38b Huestis MP, Chan L, Stuart DR, Fagnou K. Angew. Chem. Int. Ed. 2011; 50: 1338
- 38c Chen J, Song G, Pan C.-L, Li X. Org. Lett. 2010; 12: 5426
- 38d Guimond N, Fagnou K. J. Am. Chem. Soc. 2009; 131: 12050
- 38e Fukutani T, Umeda N, Hirano K, Satoh T, Miura M. Chem. Commun. 2009; 5141
- 38f Morimoto K, Hirano K, Satoh T, Miura M. Org. Lett. 2010; 12: 2068
- 38g Hyster TK, Rovis T. J. Am. Chem. Soc. 2010; 132: 10565
- 38h Mochida S, Umeda N, Hirano K, Satoh T, Miura M. Chem. Lett. 2010; 39: 744
- 38i Guoyong S, Chen D, Pan C.-L, Crabtree RH, Li X. J. Org. Chem. 2010; 75: 7487
- 38j Rakshit S, Patureau FW, Glorius F. J. Am. Chem. Soc. 2010; 132: 9585
- 38k Su Y, Zhao M, Han K, Song G, Li X. Org. Lett. 2010; 12: 5462
- 39 Too PC, Chua SH, Wong SH, Chiba S. J. Org. Chem. 2011; 76: 6159
- 40 Zhang X, Chen D, Zhao M, Zhao J, Jia A, Li X. Adv. Synth. Catal. 2011; 353: 719
- 41 Guimond N, Gorelsky SI, Fagnou K. J. Am. Chem. Soc. 2011; 133: 6449
- 42 Hyster TK, Rovis T. Chem. Commun. 2011; 47: 11846
- 43 Neely JM, Rovis T. J. Am. Chem. Soc. 2014; 136: 2735
- 44 Wang H, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 7318
- 45 Chuang S.-C, Gandeepan P, Cheng C.-H. Org. Lett. 2013; 15: 5750
- 46 Li B, Feng H, Xu S, Wang B. Chem. Eur. J. 2011; 17: 12573
- 47 Ackermann L, Lygin AV, Hofmann N. Angew. Chem. Int. Ed. 2011; 50: 6379
- 48 Li B, Ma J, Wang N, Feng H, Xu S, Wang B. Org. Lett. 2012; 14: 736
- 49 Matsuda N, Hirano K, Satoh T, Miura M. J. Org. Chem. 2012; 77: 617
- 50a Tsutsui H, Narasaka K. Chem. Lett. 1999; 28: 45
- 50b Tsutsui H, Kitamura M, Narasaka K. Bull. Chem. Soc. Jpn. 2002; 75: 1451
- 50c Kitamura M, Narasaka K. Chem. Rec. 2002; 2: 268
- 50d Narasaka K, Kitamura M. Eur. J. Org. Chem. 2005; 4505
- 51 Faulkner A, Bower JF. Angew. Chem. Int. Ed. 2012; 51: 1675
- 52 For a review, see: Smith AM. R, Hii KK. Chem. Rev. 2011; 111: 1637
- 53a Mukerjee S, Yang JW, Hoffman S, List B. Chem. Rev. 2007; 107: 5471
- 53b Melchiorre P, Marigo M, Carlone A, Bartoli G. Angew. Chem. Int. Ed. 2008; 47: 6138
- 54 Matsuda N, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2012; 51: 11827
- 55 Miura T, Morimoto M, Murakami M. Org. Lett. 2012; 14: 5214
- 56 Sandoval D, Frazier CP, Bugarin A, Read de Alaniz J. J. Am. Chem. Soc. 2012; 134: 18948
- 57a Bøgevig A, Juhl K, Kumaragurubaran N, Zhuang W, Jørgensen KA. Angew. Chem. Int. Ed. 2002; 41: 1790
- 57b List B. J. Am. Chem. Soc. 2002; 124: 5656
- 58 Tanaka T, Akagawa K, Mitsuda M, Kudo K. Adv. Synth. Catal. 2013; 355: 294
- 59 Lim YJ, Kim DY. Bull. Korean Chem. Soc. 2013; 34: 1955
For reviews, see:
For selected general reviews on C–H bond activation, see:
For selected reviews on C–H bond amination, see ref. 3b and:
For reviews, see:
For reviews, see: