α-Arylation of Amides from α-Halo Amides Using Metal-Catalyzed Cross-Coupling Reactions

E. Barde; A. Guérinot; J. Cossy

doi:10.1055/s-0037-1611358

Synthesis, Table of Contents

CC BY ND NC 4.0 · Synthesis 2019; 51(01): 178-184
DOI: 10.1055/s-0037-1611358

short review

Copyright with the author

α-Arylation of Amides from α-Halo Amides Using Metal-Catalyzed Cross-Coupling Reactions

Authors

E. Barde
A. Guérinot *

Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231, ESPCI Paris, CNRS, PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France Email: amandine.guerinot@espci.fr Email: janine.cossy@espci.fr
J. Cossy *

Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231, ESPCI Paris, CNRS, PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France Email: amandine.guerinot@espci.fr Email: janine.cossy@espci.fr

Abstract

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Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

Metal-catalyzed α-arylation of amides from α-halo amides with organometallic reagents is reviewed. The article includes Suzuki–Miyaura, Kumada–Corriu, Negishi, and Hiyama cross-coupling reactions.

1 Introduction

2 Suzuki–Miyaura Cross-Coupling

2.1 Palladium Catalysis

2.2 Nickel Catalysis

3 Kumada–Corriu Cross-Coupling

3.1 Nickel Catalysis

3.2 Iron Catalysis

3.3 Cobalt Catalysis

4 Negishi Cross-Coupling

5 Hiyama Cross-Coupling

6 Conclusion

Key words

amide - arylation - cross-coupling - metal catalysis

Full Text

References

References

Selected book and reviews:

1a In The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry and Materials Science . Greenberg A, Breneman CM, Liebman JF. Wiley; New York: 2000
1b Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606
1c Allen CL, Williams JM. J. Chem. Soc. Rev. 2011; 40: 3405
1d Pattabiraman VR, Bode JW. Nature (London) 2011; 480: 471
1e Zhang D.-W, Zhao X, Hou J.-L, Li Z.-T. Chem. Rev. 2012; 112: 5271
1f de Figueiredo RM, Suppo J.-S, Campagne J.-M. Chem. Rev. 2016; 116: 12029 ; and references therein

2a Owen RT, Castañer R, Bolós J, Estivill C. Drugs Future 2009; 34: 5
2b Fañanás-Mastral M, Teichert JF, Fernández-Salas JA, Heijnen D, Feringa BL. Org. Biomol. Chem. 2013; 11: 4521

3 Akisanya J, Parkins AW, Steed JW. Org. Process Res. Dev. 1998; 2: 274 ; and references therein

See for example:

4a Jullian V. Synthesis 1997; 1091
4b Honda T, Namiki H, Satoh F. Org. Lett. 2001; 3: 631
4c Wang M.-X, Zhao S.-M. Tetrahedron Lett. 2002; 43: 6617

Selected reviews:

5a Johansson CC. C, Colacot TJ. Angew. Chem. Int. Ed. 2010; 49: 676
5b Bellina F, Rossi R. Chem. Rev. 2010; 110: 1082

See for example:

6a Lee S, Beare NA, Hartwig JF. J. Am. Chem. Soc. 2001; 123: 8410
6b Moradi WA, Buchwald SL. J. Am. Chem. Soc. 2001; 123: 7996
6c Hamann BH, Hartwig JF. J. Am. Chem. Soc. 1997; 119: 12382
6d Palucki M, Buchwald SL. J. Am. Chem. Soc. 1997; 119: 11108
6e Ahman J, Wolfe JP, Trautman MV, Palucki M, Buchwald SL. J. Am. Chem. Soc. 1998; 120: 1918

7 Bordwell FG. Acc. Chem. Res. 1988; 21: 456
8 Shaughnessy KH, Hamann BH, Hartwig JF. J. Org. Chem. 1998; 63: 6546

For intramolecular arylations, see:

9a Lee S, Hartwig JF. J. Org. Chem. 2001; 66: 3402
9b Zhang TY, Zhang H. Tetrahedron Lett. 2002; 43: 193
9c Solé D, Serrano O. J. Org. Chem. 2008; 73: 9372
9d Pan X, Wilcox CS. J. Org. Chem. 2010; 75: 6445

10 For the α-arylation of oxindoles, see: Durbin MJ, Willis MC. Org. Lett. 2008; 10: 1413
11 For a more general method of α-arylation of amide enolates, see: Zheng B, Jia T, Walsh PJ. Adv. Synth. Catal. 2014; 356: 165

Selected examples:

12a De Filippis A, Gomez-Pardo D, Cossy J. Org. Lett. 2003; 5: 3037
12b Cossy J, De Filippis A, Gomez-Pardo D. Synlett 2003; 2171
12c De Filippis A, Gomez-Pardo D, Cossy J. Tetrahedron 2004; 60: 9757
12d Michon C, Béthegnies A, Capet F, Roussel P, De Filippis A, Gomez-Pardo D, Cossy J, Agbossou-Niedercorn F. Eur. J. Org. Chem. 2013; 4979

13a Hama T, Liu X, Culkin DA, Hartwig JF. J. Am. Chem. Soc. 2003; 125: 11176
13b Hama T, Culkin DA, Hartwig JF. J. Am. Chem. Soc. 2006; 128: 4976

14 Hlavinka ML, Hagadorn JR. Organometallics 2007; 26: 4105

For other methods allowing the α-arylation of amides, see:

15a Alonso RA, Rodriguez CH, Rossi RA. J. Org. Chem. 1989; 54: 5983
15b Hirner S, Somfai P. J. Org. Chem. 2009; 74: 7798
15c Romero O, Castro A, Terán JL, Gnecco D, Orea ML, Mendoza A, Flores M, Roa LF, Juárez JR. Tetrahedron Lett. 2011; 52: 5947
15d Peng B, Geerdink D, Farès C, Maulide N. Angew. Chem. Int. Ed. 2014; 53: 5462
15e Takeda N, Futaki E, Kobori Y, Ueda M, Miyata O. Angew. Chem. Int. Ed. 2017; 56: 16342

16a Metal-Catalyzed Cross-Coupling Reactions and More . de Meijere A, Bräse S, Oestreich M. Wiley; Hoboken: 2014
16b Science of Synthesis: Cross-Coupling and Heck-Type Reactions. Thieme; Stuttgart: 2013

17 Gooßen LJ. Chem. Commun. 2001; 669
18 Duan Y.-Z, Deng M.-Z. Tetrahedron Lett. 2003; 44: 3423
19 Zimmermann B, Dzik WI, Himmler T, Gooßen LJ. J. Org. Chem. 2011; 76: 8107
20 Traister KM, Barcellos T, Molander GA. J. Org. Chem. 2013; 78: 4123
21 Lin B.-L, Liu L, Fu Y, Luo S.-W, Chen Q, Guo Q.-X. Organometallics 2004; 23: 2114
22 Liu C, He C, Shi W, Chen M, Lei A. Org. Lett. 2007; 9: 5601
23 Lundin PM, Fu GC. J. Am. Chem. Soc. 2010; 132: 11027
24 Xiao Y.-L, Guo W.-H, He G.-Z, Pan Q, Zhang X. Angew. Chem. Int. Ed. 2014; 53: 9909

25a Blackburn CM, England DA, Kolkmann F. J. Chem. Soc., Chem. Commun. 1981; 930
25b Blackburn CM, Kent DE, Kolkmann F. J. Chem. Soc., Perkin Trans. 1 1984; 1119

26 Tarui A, Miyata E, Tanaka A, Sato K, Omote M, Ando A. Synlett 2015; 26: 55
27 Tarui A, Kondo S, Sato K, Omote M, Minami H, Miwa Y, Ando A. Tetrahedron 2013; 69: 1559

28a Bauer I, Knölker H.-J. Chem. Rev. 2015; 115: 3170
28b Sherry BD, Fürstner A. Acc. Chem. Res. 2008; 41: 1500
28c Mako TL, Byers JA. Inorg. Chem. Front. 2016; 3: 766
28d Guérinot A, Cossy J. Top. Curr. Chem. 2016; 49: 374

29 Jin M, Nakamura M. Chem. Lett. 2011; 40: 1012
30 Barde E, Guérinot A, Cossy J. Org. Lett. 2017; 19: 6160
31 Tarui A, Saori S, Sato K, Omote M, Ando A. Org. Lett. 2016; 18: 1128
32 Strotman NA, Sommer S, Fu GC. Angew. Chem. Int. Ed. 2007; 46: 3556