Regioselective Diboron-Mediated Semireduction of Terminal Allenes

Abstract

A method for the regioselective reduction of the terminal double bond of 1,1-disubstituted allenes has been developed. In the presence of a palladium catalyst, tetrahydroxydiboron and stoichiometric water, allene semireduction proceeds in high yield to afford Z-alkenes selectively.

Key words

diboron-mediated - allenes - hydrogenation - semireduction

• References

• 1a Hoffmann-Röder A, Krause N. Angew. Chem. Int. Ed. 2004; 43: 1196
• 1b Yu S, Ma S. Angew. Chem. Int. Ed. 2012; 51: 3074
• 1c Yu S, Ma S. Chem. Commun. 2011; 47: 5384
• 2 Chen Z, Dong VM. Nature Commun. 2017; 784
• 3 Nagendrappa G, Srivastava RK, Devaprabhakara D. J. Org. Chem. 1970; 35: 347
• 4a Okuyama T, Toyoshima K, Fueno T. J. Org. Chem. 1980; 45: 1604
• 4b Nagendrappa G, Devaprabhakara D. Tetrahedron Lett. 1970; 11: 4243
• 5 Montury M, Goré J. Tetrahedron Lett. 1980; 21: 51
• 6 Fleming I, Rowley M, Cuadrado P, González-Nogal AM, Pulido FJ. Tetrahedron 1989; 45: 413
• 7 Bhagwat MM, Devaprabhakara D. Tetrahedron Lett. 1972; 13: 1391
• 8 Guo H, Zheng Z, Yu F, Ma S, Holuigue A, Tromp DS, Elsevier CJ, Yu Y. Angew. Chem. Int. Ed. 2006; 45: 4997
• 9 Adler P, Gomes F, Fadel A, Rabasso N. Eur. J. Org. Chem. 2013; 7546
• 10a Thorpe SB, Guo X, Santos WL. Chem. Commun. 2011; 47: 424
• 10b Guo X, Nelson AK, Slebodnick C, Santos WL. ACS Catal. 2015; 5: 2172
• 10c Pashikanti S, Calderone JA, Nguyen MK, Sibley CD, Santos WL. Org. Lett. 2016; 18: 2443
• 11 Cummings SP, Le T.-N, Fernandez GE, Quiambao LG, Stokes BJ. J. Am. Chem. Soc. 2016; 138: 6107
• 12 Ojha DP, Gadde K, Prabhu KR. Org. Lett. 2016; 18: 5062
• 13a Wei Y, Zhao C, Xuan Q, Song Q. Org. Chem. Front. 2017; 4: 2291
• 13b Liu S, Zhou Y, Sui Y, Liu H, Zhou H. Org. Chem. Front. 2017; 4: 2175
• 13c Zhou Y, Zhou H, Liu S, Pi D, Shen G. Tetrahedron 2017; 73: 3898
• 14a Xia Y.-T, Sun X.-T, Zhang L, Luo K, Wu L. Chem. Eur. J. 2016; 22: 17151
• 14b Xuan Q, Song Q. Org. Lett. 2016; 18: 4250
• 15 Du H.-C, Simmons N, Faver JC, Yu Z, Palaniappan M, Riehle K, Matzuk MM. Org. Lett. 2019; 21: 2194
• 16 Kawai Y, Inaba Y, Tokitoh N. Tetrahedron: Asymmetry 2001; 12: 309
• 17 Zhu N, Zhao J, Bao H. Chem. Sci. 2017; 8: 2081
• 18 Hornback JM, Barrows RD. J. Org. Chem. 1982; 47: 4285
• 19 Silva AR, Polo EC, Martins NC, Correia CR. D. Adv. Synth. Catal. 2018; 360: 346
• 20 Tanaka S, Watanabe K, Tanaka Y, Hattori T. Org. Lett. 2016; 18: 2576
• 21 Rong G, Liu D, Lu L, Yan H, Zheng Y, Chen J, Mao J. Tetrahedron 2014; 70: 5033
• 22 Suzuki K, Kobayashi T, Takenobu N, Hori Y, Hagiwara T. EP 1167372(A1), 2002
• 23 Barluenga J, Florentino L, Aznar F, Valdés C. Org. Lett. 2011; 13: 510
• 24 Gärtner D, Welther A, Rad BR, Wolf R, Jacobi von Wangelin A. Angew. Chem. Int. Ed. 2014; 53: 3722