Recent Progress in Base Metal Catalyzed (Transfer) Hydrogenative Couplings of Carbonyls with π-Unsaturated Compounds

Abstract

Catalytic hydrogenative coupling of carbonyls with π-unsaturated compounds employing hydrogen gas or H donors as terminal reductants is an attractive method for C–C bond formation. Herein, we give a brief review on its development and highlight recent advances on the use of base metal catalysts, such as nickel and iron.

1 Introduction

2 Noble Metal Catalyzed (Transfer) Hydrogenative Couplings of Carbonyls with π-Unsaturated Compounds

3 Nickel-Catalyzed Transfer Hydrogenative Couplings of Paraformaldehyde with π-Unsaturated Compounds

4 Iron-Catalyzed Transfer Hydrogenative Couplings of Carbonyls with π-Unsaturated Compounds

5 Conclusion

Key words

iron catalysis - unactivated aldehydes - simple alkenes - hydrogen transfer - hydrogenative coupling

• References


For reviews, see:
• 1a Montgomery J. Acc. Chem. Res. 2000; 33: 467
• 1b Montgomery J. Angew. Chem. Int. Ed. 2004; 43: 3890
• 1c Moslin RM, Miller-Moslin K, Jamison TF. Chem. Commun. 2007; 4441
• 1d Jeganmohan M, Cheng CH. Chem. Eur. J. 2008; 14: 10876
• 1e Ng SS, Ho CY, Schleicher KD, Jamison TF. Pure Appl. Chem. 2008; 80: 929
• 1f Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
• 2 Molander GA, Hoberg JO. J. Am. Chem. Soc. 1992; 114: 3123
• 3 Kokubo K, Miura M, Nomura M. Organometallics 1995; 14: 4521
• 4 Jang HY, Huddleston RR, Krische MJ. J. Am. Chem. Soc. 2002; 124: 15156

For reviews, see:
• 5a Jang HY, Krische MJ. Acc. Chem. Res. 2004; 37: 653
• 5b Skucas E, Ngai MY, Komanduri V, Krische MJ. Acc. Chem. Res. 2007; 40: 1394
• 5c Bower JF, Kim IS, Patman RL, Krische MJ. Angew. Chem. Int. Ed. 2009; 48: 34
• 5d Ketcham JM, Shin I, Montgomery TP, Krische MJ. Angew. Chem. Int. Ed. 2014; 53: 9142
• 6 Jang H.-Y, Huddleston RR, Krische MJ. J. Am. Chem. Soc. 2002; 124: 15156
• 7 Huddleston RR, Jang H.-Y, Krische MJ. J. Am. Chem. Soc. 2003; 125: 11488
• 8 Jang H.-Y, Huddleston RR, Krische MJ. J. Am. Chem. Soc. 2004; 126: 4664
• 9 Ngai M.-Y, Barchuk A, Krische MJ. J. Am. Chem. Soc. 2007; 129: 280
• 10 Skucas E, Bower JF, Krische MJ. J. Am. Chem. Soc. 2007; 129: 12678
• 11 Kim IS, Ngai M.-Y, Krische MJ. J. Am. Chem. Soc. 2008; 130: 6340
• 12 Bower JF, Patman RL, Krische MJ. Org. Lett. 2008; 10: 1033
• 13 Cho C.-W, Skucas E, Krische MJ. Organometallics 2007; 26: 3860
• 14 Hong YT, Barchuk A, Krische MJ. Angew. Chem. Int. Ed. 2006; 45: 6885
• 15 Yamaguchi E, Mowat J, Luong T, Krische MJ. Angew. Chem. Int. Ed. 2013; 52: 8428
• 16 Bausch CC, Patman RL, Breit B, Krische MJ. Angew. Chem. Int. Ed. 2011; 50: 5687
• 17 Köpfer A, Sam B, Breit B, Krische MJ. Chem. Sci. 2013; 4: 1876
• 18 Chuah GK, Jaenicke S, Zhu YZ, Liu SH. Curr. Org. Chem. 2006; 10: 1639
• 19 Radianingtyas H, Wright PC. FEMS Microbiol. Rev. 2003; 27: 593
• 20 Zheng YL, Liu YY, Wu YM, Wang YX, Lin YT, Ye M. Angew. Chem. Int. Ed. 2016; 55: 6315