Construction of α-Alkylated Amines by Iridium Complex-Catalyzed One-Step Transfer Hydrogenation of C=C and C=N Bonds

Abstract

Hydrogenation of C=C bond and reductive amination are important transformations utilized in chemistry. An environmentally friendly, efficient, and facile one-pot transfer hydrogenation of C=C bond of enones and reductive amination of C=N bond of imines are reported using iridium complex as catalysts and formic acid as hydrogen source in aqueous medium. In this catalytic system, a wide range of α-alkylated amines were obtained in excellent yields by one-pot transfer hydrogenation of C=C bond and reductive amination. The practical application of this protocol is characterized by gram-scale transformation.

Key words

transfer hydrogenation - iridium complex - reductive amination - enones

• References

• 1a Kim H, Chang S. ACS Catal. 2016; 6: 2341
• 1b Jiao J, Murakami K, Itami K. ACS Catal. 2016; 6: 610
• 1c Park Y, Kim Y, Chang S. Chem. Rev. 2017; 117: 9247
• 1d Wang Y, Furukawa S, Fu X, Yan N. ACS Catal. 2020; 10: 311
• 1e Trowbridge A, Walton SA, Guant MJ. Chem. Rev. 2020; 120: 2613
• 2a Shinde GB, Niphade NC, Deshmukh SP, Toche RB, Mathad VT. Org. Process Res. Dev. 2011; 15: 455
• 2b Rische T, Eibracht P. Tetrahedron 1999; 55: 1915
• 3a Mercea DM, Howlett MG, Piascik AD, Scott DJ, Steven A, Ashley AE, Fuchter MJ. Chem. Commun. 2019; 55: 7077
• 3b Graves CR, Scheidt KA, Nguyen ST. Org. Lett. 2006; 8: 1229
• 4a Tang R, Shao Z, Wang J, Liu Z, Li Y.-M, Shen Y. J. Org. Chem. 2019; 84: 8177
• 4b Hensel A, Nagura K, Delvos LB, Oestreich M. Angew. Chem. Int. Ed. 2014; 53: 4964
• 4c Adrian JC, Barkin JL, Fox RJ, Chick JE, Hunter AD, Nicklow RA. J. Org. Chem. 2000; 65: 6264
• 5a Dçrfler J, Doye S. Angew. Chem. Int. Ed. 2013; 52: 1806
• 5b Dçrfler J, Preuß T, Schischko A, Schmidtmann M, Doye S. Angew. Chem. Int. Ed. 2014; 53: 7918
• 5c Kaiser D, Tona V, Gonçalves CR, Shaaban S, Oppedisano A, Maulide N. Angew. Chem. Int. Ed. 2019; 58: 14639
• 5d Hanna S, Holder JC, Hartwig JF. Angew. Chem. Int. Ed. 2019; 58: 3368
• 5e Chen C, Dong X.-Q, Zhang X. Org. Chem. Front. 2016; 3: 1359
• 6a Knowles WS. Angew. Chem. Int. Ed. 2002; 41: 1998
• 6b Noyori R. Adv. Synth. Catal. 2003; 345: 15
• 6c Wang D.-S, Chen Q.-A, Lu S.-M, Zhou Y.-G. Chem. Rev. 2012; 112: 2557
• 6d Lan X, Wang T. ACS Catal. 2020; 10: 2764
• 7a Astruc D, Wang D. Chem. Rev. 2015; 115: 6621
• 7b Bigler R, Mezzetti A. Org. Process Res. Dev. 2016; 20: 253
• 7c Tan Z, Yang J, Liang Y, Jiang H, Zhang M. iScience 2020; 23: 101003
• 8a Ai W, Zhong R, Liu X, Liu Q. Chem. Rev. 2019; 119: 2876
• 8b Alig L, Fritz M, Schneider S. Chem. Rev. 2019; 119: 2681
• 9a Tang W, Zhang X. Chem. Rev. 2003; 103: 3029
• 9b Xie J.-H, Zhu S.-F, Zhou Q.-L. Chem. Rev. 2011; 111: 1713
• 9c Busacca CA, Fandrick DR, Song JJ, Senanayake CH. Adv. Synth. Catal. 2011; 353: 1825
• 9d Wang D.-S, Chen Q.-A, Lu S.-M, Zhou Y.-G. Chem. Rev. 2012; 112: 2557
• 9e Verendel JJ, Pàmies O, Diéguez M, Andersson PG. Chem. Rev. 2014; 114: 2130
• 9f Zhang Z, Butt NA, Zhang W. Chem. Rev. 2016; 116: 14769
• 9g Hayler JD, Leahy DK, Simmons EM. Organometallics 2019; 38: 36
• 10a Nugent TC, El-Shazly M. Adv. Synth. Catal. 2010; 352: 753
• 10b Wakchaure VN, Zhou J, Hoffmann S, List B. Angew. Chem. Int. Ed. 2010; 49: 4612
• 10c Savile CK, Janey JM, Mundorff EC, Moore JC, Tam S, Jarvis WR, Colbeck JC, Krebber A, Fleitz FJ, Brands J, Devine PN, Huisman GW, Hughes GJ. Science 2010; 329: 305
• 10d Wang C, Pettman A, Bacsa J, Xiao J. Angew. Chem. Int. Ed. 2010; 49: 7548
• 10e Jagadeesh RV, Murugesan K, Alshammari AS, Neumann H, Pohl M.-M, Radnik J, Beller M. Science 2017; 358: 326
• 10f Gallardo-Donaire J, Hermsen M, Wysocki J, Ernst M, Rominger F, Trapp O, Hashmi AS. K, Schäfer A, Comba P, Schaub T. J. Am. Chem. Soc. 2018; 140: 355
• 10g Mayol O, Bastard K, Beloti L, Frese A, Turkenburg JP, Petit J.-L, Mariage A, Debard A, Pellouin V, Perret A, Berardinis V, Zaparucha A, Groqan G, Vergne-Vaxelaire C. Nat. Catal. 2019; 2: 324
• 11a Luo N, Liao J, Ouyang L, Wen H, Zhong Y, Liu J, Tang W, Luo R. Organometallics 2020; 39: 165
• 11b Luo N, Liao J, Ouyang L, Wen H, Liu J.-T, Tang W, Luo R. Organometallics 2019; 38: 3025
• 11c Lou R, Cheng G, Wei Y, Deng R, Huang M, Liao J. Organometallics 2018; 37: 1652
• 11d Luo N, Zhong Y, Liu J-T, Ouyang L, Luo R. Synthesis 2020; 52: 3439
• 11e Ouyang L, Xia Y, Liao J, Luo R. Eur. J. Org. Chem. 2020; 6387
• 12 Chen Y, Pan Y, He Y.-M, Fan Q.-H. Angew. Chem. Int. Ed. 2019; 58: 16831
• 13 Yuan S, Gao G, Wang L, Liu C, Wan L, Huang H, Geng H, Chang M. Nat. Commun. 2020; 11: 621
• 14 Lei Q, Wei Y, Talwar D, Wang C, Xue D, Xiao J. Chem. Eur. J. 2013; 19: 4021
• 15a Mellmann D, Sponholz P, Junge H, Beller M. Chem. Soc. Rev. 2016; 45: 3954
• 15b Li J, Li J, Zhang D, Liu C. ACS Catal. 2016; 6: 4746
• 16a Storer RI, Carrera DE, Ni Y, MacMillan DW. C. J. Am. Chem. Soc. 2006; 128: 84
• 16b Hoffmann S, Nicoletti M, List B. J. Am. Chem. Soc. 2006; 128: 13074
• 16c Aberg JB, Samec JS. M, Backvall JE. Chem. Commun. 2006; 2771
• 16d Li C, Wang C, Villa-Marcos B, Xiao J. J. Am. Chem. Soc. 2008; 130: 14450
• 16e Zhou H, Li Z, Wang Z, Wang T, Xu L, He Y, Fan QH, Pan J, Gu L, Chan AS. C. Angew. Chem. Int. Ed. 2008; 47: 8464
• 17a Wu X, Liu J, Tommaso DD, Iggo JA, Catlow CR. A, Bacsa J, Xiao JA. Chem. Eur. J. 2008; 14: 7699
• 17b Pavlova A, Meijer EJ. ChemPhysChem 2012; 13: 3492
• 18a Liu J.-T, Yang S, Tang W, Yang Z, Xu J. Green Chem. 2018; 20: 2118
• 18b Li J, Tang W, Ren D, Xu J, Yang Z. Green Chem. 2019; 21: 2088
• 19a Brieger G, Nestrick TJ. Chem. Rev. 1974; 74: 567
• 19b Johnstone RA. W, Wilby AH, Entwistle ID. Chem. Rev. 1985; 85: 129
• 19c Zassinovich G, Mestroni G, Gladiali S. Chem. Rev. 1992; 92: 1051
• 20a Wang C, Xiao J. Chem. Commun. 2017; 53: 3399
• 20b Wang C, Chen H.-YT, Basca J, Catlow CR. A, Xiao J. Dalton Trans. 2013; 42: 935
• 20c Koike T, Ikariya T. Adv. Synth. Catal. 2004; 346: 37
• 20d Dobereiner GE, Nova A, Schley ND, Hazari N, Miller S, Eisenstein JO, Crabtree RH. J. Am. Chem. Soc. 2011; 133: 7547
• 20e Wang S, Huang H, Bruneau C, Fischmeister C. ChemSusChem 2019; 12: 2350
• 21a Abdukader A, Jin H, Cheng Y, Zhu C. Tetrahedron Lett. 2014; 55: 4172
• 21b Liu Y.-Y, Liang D, Lu L.-Q, Xaio W.-J. Chem. Commun. 2019; 55: 4853
• 21c Saitoa K, Akiyama T. Chem. Commun. 2012; 48: 4573
• 21d Haak E, Bytschkov I, Doye S. Angew. Chem. Int. Ed. 1999; 38: 3389
• 21e Murugan S, Siba PM, Palmurukan MR, Ekambaram B. Org. Lett. 2019; 21: 8899
• 21f Kouznetsov V, Urbina GJ. M, Stashenko E. Acta Hort. 1999; 501: 133