Catalytic α-Alkylation/Reduction of Ketones with Primary Alcohols To Furnish Secondary Alcohols

Abstract

The formation of secondary alcohol products via a tandem α-alkylation/transfer hydrogenation of ketones with primary alcohols is a little explored reaction with unrealized potential for green synthesis. This review covers the current literature in the field, including asymmetric versions of the reaction, and outlines future possibilities and challenges for the methodology.

1 Introduction

2 Formation of Racemic Alcohols

3 Formation of Enantiomerically Enriched Alcohols

4 Conclusions

Key words

α-alkylation - transfer hydrogenation - ketone - alcohol - catalysis - tandem process

• References


For an overview, see:
• 1a Stoltz BM, Bennett NB, Duquette DC, Goldberg AF. G, Liu Y, Loewinger MM, Reeves CM In Comprehensive Organic Synthesis . 2nd ed., Vol. 3; Knochel P, Molander GA. Elsevier; Amsterdam: 2014: 1
• 1b Stoltz BM, Mohr JT In Science of Synthesis: Stereoselective Synthesis . Vol. 3. Evans PA. Georg Thieme Verlag; Stuttgart: 2011: 615
• 1c Alba A.-N, Viciano M, Rios R. ChemCatChem 2009; 1: 437
• 1d Merritt EA, Olofsson B. Synthesis 2011; 517
• 1e Culkin DA, Hartwig JF. Acc. Chem. Res. 2003; 36: 234
• 2 Constable DJ. C, Dunn PJ, Hayler JD, Humphrey GR, Leazer JL, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells A, Zaks A, Zhang TY. Green Chem. 2007; 9: 411
• 3a Crabtree RH. Organometallics 2011; 30: 17
• 3b Watson AJ. A, Williams JM. J. Science (Washington, D.C.) 2010; 329: 635

For reviews on the topic see, e.g.:
• 4a Shimizu K.-i. Catal. Sci. Technol. 2015; 5: 1412
• 4b Obora Y. ACS Catal. 2014; 4: 3972
• 4c Cui X, Zhang Y, Shi F, Deng Y. Chem. Eur. J. 2011; 17: 1021
• 4d Saidi O, Williams JM. J. Top. Organomet. Chem. 2011; 34: 77
• 4e Dobereiner GE, Crabtree RH. Chem. Rev. 2009; 110: 681
• 4f Nixon TD, Whittlesey MK, Williams JM. J. Dalton Trans. 2009; 753
• 4g Guillena G, Ramon DJ, Yus M. Angew. Chem. Int. Ed. 2007; 46: 2358
• 4h Hamid MH. S. A, Slatford PA, Williams JM. J. Adv. Synth. Catal. 2007; 349: 1555
• 5a Lee D.-H, Kwon K.-H, Yi CS. Science (Washington, D. C.) 2011; 333: 1613

For recent reviews on the topic see also, e.g.:
• 5b Ketcham JM, Shin I, Montgomery TP, Krische MJ. Angew. Chem. Int. Ed. 2014; 53: 9142
• 5c Dechert-Schmitt A.-MR, Schmitt DC, Gao X, Itoh T, Krische MJ. Nat. Prod. Rep. 2014; 31: 504
• 5d Moran J, Krische MJ In Asymmetric Synthesis II . Christmann M, Bräse S. Wiley-VCH; Weinheim: 2012: 187
• 5e Moran J, Krische MJ In Sustainable Catalysis . Dunn PJ, Hii KK, Krische MJ, Williams MT. John Wiley & Sons; Hoboken: 2013: 363
• 6a Naskar S, Bhattacharjee M. Tetrahedron Lett. 2007; 48: 465
• 6b Sharma A, Kumar V, Sinha AK. Adv. Synth. Catal. 2006; 348: 354
• 7a Chen S.-j, Lu G.-p, Cai C. RSC Adv. 2015; 5: 13208
• 7b Ding B, Zhang Z, Liu Y, Sugiya M, Imamoto T, Zhang W. Org. Lett. 2013; 15: 3690
• 8 Li X, Li L, Tang Y, Zhong L, Cun L, Zhu J, Liao J, Deng J. J. Org. Chem. 2010; 75: 2981
• 9a Bizet V, Pannecoucke X, Renaud J.-L, Cahard D. Angew. Chem. Int. Ed. 2012; 51: 6467
• 9b Ahlsten N, Lundberg H, Martin-Matute B. Green Chem. 2010; 12: 1628
• 9c Cadierno V, García-Garrido SE, Gimeno J, Varela-Álvarez A, Sordo JA. J. Am. Chem. Soc. 2006; 128: 1360
• 9d Trost BM, Kulawiec RJ. J. Am. Chem. Soc. 1993; 115: 2027

For recent reviews see, e.g.:
• 10a Wang D, Astruc D. Chem. Rev. 2015; 115: 6621
• 10b Wu X, Xiao J In Comprehensive Organic Synthesis . 2nd ed., Vol. 8; Knochel P, Molander GA. Elsevier; Amsterdam: 2014: 198
• 10c Ito J.-i, Nishiyama H. Tetrahedron Lett. 2014; 55: 3153
• 10d Zaidlewicz M, Pakulski MM In Science of Synthesis: Stereoselective Synthesis . Vol. 2. Molander GA. Georg Thieme Verlag; Stuttgart: 2011: 59
• 10e Klomp D, Hanefeld U, Peters JA In The Handbook of Homogeneous Hydrogenation . de Vries JG, Elsevier CJ. Wiley-VCH; Weinheim: 2008: 585
• 11a Cotarca L, Verzini M, Volpicelli R. Chim. Oggi 2014; 32: 36
• 11b Komiya S, Shimizu H, Nagasaki I In Comprehensive Chirality . Vol. 9. Carreira EM, Yamamoto H. Elsevier; Amsterdam: 2012: 83
• 12 Meerwein H, Schmidt R. Justus Liebigs Ann. Chem. 1925; 444: 221
• 13 Verley A. Bull. Soc. Chim. Fr. 1925; 37: 537
• 14 Ponndorf W. Angew. Chem. 1926; 29: 138
• 15 Oppenauer RV. Recl. Trav. Chim. Pays-Bas 1937; 56: 137
• 16a Castellani CB, Carugo O, Perotti A, Sacchi D, Invernizzi AG, Vidari G. J. Mol. Catal. 1993; 85: 65
• 16b Okano T, Matsuoka M, Konishi H, Kiji J. Chem. Lett. 1987; 181
• 16c Namy JL, Souppe J, Collin J, Kagan HB. J. Org. Chem. 1984; 49: 2045
• 17 For a review on the topic see: Nishide K, Node M. Chirality 2002; 14: 759
• 18 Bäckvall J.-E. J. Organomet. Chem. 2002; 652: 105

For reviews see, e.g.:
• 19a Foubelo F, Najera C, Yus M. Tetrahedron: Asymmetry 2015; 26: 769
• 19b Ito J.-i, Nishiyama H. Tetrahedron Lett. 2014; 55: 3153
• 19c Štefane B, Požgan F. Catal. Rev. 2014; 56: 82
• 19d Obora Y, Ishii Y. Synlett 2011; 30
• 19e Malacea R, Poli R, Manoury E. Coord. Chem. Rev. 2010; 254: 729
• 19f Kitamura M, Noyori R In Ruthenium in Organic Synthesis . Murahashi S.-I. Wiley-VCH; Weinheim: 2005: 3

For recent reviews, see:
• 20a Morris RH. Acc. Chem. Res. 2015; 48: 1494
• 20b Li Y.-Y, Yu S.-L, Shen W.-Y, Gao J.-X. Acc. Chem. Res. 2015; 48: 2587
• 21a Shvo Y, Czarkie D, Rahamim Y, Chodosh DF. J. Am. Chem. Soc. 1986; 108: 7400
• 21b Warner MC, Casey CP, Bäckvall J.-E. Top. Organomet. Chem. 2011; 37: 85 ; and references therein
• 22a Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R. J. Am. Chem. Soc. 1995; 117: 7562
• 22b Václavík J, Kačer P, Kuzma M, Červený L. Molecules 2011; 16: 5460 ; and references therein

See, e.g.:
• 23a Wakeham RJ, Morris JA, Williams JM. J. ­ChemCatChem 2015; 7: 4039
• 23b Slagbrand T, Kivijärvi T, Adolfsson H. ChemCatChem 2015; 7: 3445
• 23c Lundberg H, Adolfsson H. Tetrahedron Lett. 2011; 52: 2754
• 23d Zweifel T, Naubron J.-V, Büttner T, Ott T, Grützmacher H. Angew. Chem. Int. Ed. 2008; 47: 3245
• 23e Maytum HC, Tavassoli B, Williams JM. J. Org. Lett. 2007; 9: 4387
• 24a Kwon MS, Kim N, Seo SH, Park IS, Cheedrala RK, Park J. Angew. Chem. Int. Ed. 2005; 44: 6913
• 24b Li J, Zhang W, Wang F, Jiang M, Dong X, Zhao W. Chin. J. Chem. 2012; 30: 2363
• 24c Dixit M, Mishra M, Joshi PA, Shah DO. Catal. Commun. 2013; 33: 80
• 24d Ogawa S, Obora Y. Chem. Commun. 2014; 50: 2491
• 24e Xu G, Li Q, Feng J, Liu Q, Zhang Z, Wang X, Zhang X, Mu X. ChemSusChem 2014; 7: 105
• 24f Taguchi K, Nakagawa H, Hirabayashi T, Sakaguchi S, Ishii Y. J. Am. Chem. Soc. 2004; 126: 72
• 24g Yan F.-X, Zhang M, Wang X.-T, Xie F, Chen M.-M, Jiang H. Tetrahedron 2014; 70: 1193
• 25 Cho CS. J. Mol. Catal. A: Chem. 2005; 240: 55
• 26 Cho CS, Kim BT, Kim T.-J, Shim SC. Tetrahedron Lett. 2002; 43: 7987
• 27 Cho CS, Kim BT, Kim T.-J, Shim SC. J. Org. Chem. 2001; 66: 9020
• 28 Cho CS. J. Mol. Catal. A: Chem. 2007; 267: 49
• 29 Ohkuma T, Ooka H, Hashiguchi S, Ikariya T, Noyori R. J. Am. Chem. Soc. 1995; 117: 2675
• 30a Nishiguchi T, Tachi K, Fukuzumi K. J. Am. Chem. Soc. 1972; 94: 8916
• 30b Nishiguchi T, Fukuzumi K. J. Am. Chem. Soc. 1974; 96: 1893
• 30c Imai H, Nishiguchi T, Fukuzumi K. J. Org. Chem. 1976; 41: 665
• 30d Cho CS, Shim SC. J. Organomet. Chem. 2006; 691: 4329
• 31 Martinez R, Brand GJ, Ramon DJ, Yus M. Tetrahedron Lett. 2005; 46: 3683
• 32 Martinez R, Ramon DJ, Yus M. Tetrahedron 2006; 62: 8988
• 33 Satyanarayana P, Reddy GM, Maheswaran H, Kantam ML. Adv. Synth. Catal. 2013; 355: 1859
• 34 Liao S, Yu K, Li Q, Tian H, Zhang Z, Yu X, Xu Q. Org. Biomol. Chem. 2012; 10: 2973
• 35 Xu Q, Chen J, Tian H, Yuan X, Li S, Zhou C, Liu J. Angew. Chem. Int. Ed. 2014; 53: 225
• 36a Xu Q, Li Q, Zhu X, Chen J. Adv. Synth. Catal. 2013; 355: 73
• 36b Xu Q, Chen J, Liu Q. Adv. Synth. Catal. 2013; 355: 697
• 37 Onodera G, Nishibayashi Y, Uemura S. Angew. Chem. Int. Ed. 2006; 45: 3819
• 38 Kovalenko OO, Lundberg H, Hübner D, Adolfsson H. Eur. J. Org. Chem. 2014; 6639