Nickel-Catalyzed Multicomponent Coupling of Alkyne, Buta-1,3-diene, and Dimethylzinc under Carbon Dioxide

Abstract

A nickel catalyst promoted the coupling of alkynes with buta-1,3-diene and dimethylzinc under carbon dioxide to provide (5E,8Z)-2-vinyldeca-5,8-dienoic acids with high regio- and stereo­selectivity.

Key words

nickel - alkyne - carbon dioxide - butadiene - dimethyl­zinc

• References

• 1a Hyster TK, Ruhl KE, Rovis T. J. Am. Chem. Soc. 2013; 135: 5364
• 1b Zhang M, Neumann H, Meller M. Angew. Chem. Int. Ed. 2013; 52: 597
• 1c Qian W, Wang H, Allen J. Angew. Chem. Int. Ed. 2013; 52: 10992
• 1d Partridge KM, Bader SJ, Buchan ZA, Taylor CE. Angew. Chem. Int. Ed. 2013; 52: 13647
• 1e Tan B.-H, Dong J, Yoshikai N. Angew. Chem. Int. Ed. 2012; 51: 9610
• 1f Xiong W, Xin Y, Zhao J, Zhu S. Synthesis 2011; 1142
• 1g Zhu J, Bienaymé H. Multicomponent Reactions . Wiley-VCH; Weinheim: 2005
• 1h Tamaru Y. Modern Organonickel Chemistry . Wiley-VCH; Weinheim: 2005
• 2a Hamilton J, Sarlah D, Carreira EM. Angew. Chem. Int. Ed. 2013; 52: 7532
• 2b Reznichnko AL, Hultzsch KC. Top. Organomet. Chem. 2013; 51
• 2c Gu Z, Vollhardt KP. C. Synthesis 2013; 45: 2469
• 2d Mori T, Nakamura T, Onodera G, Kimura M. Synthesis 2012; 44: 2333
• 2e Schmeier TJ, Nova A, Hazari N, Maseras F. Chem. Eur. J. 2012; 18: 6915
• 2f Takimoto M, Mizuno T, Mori M, Sato Y. Tetrahedron 2006; 62: 7589
• 2g Takimoto M, Shimizu K, Mori M. Org. Lett. 2001; 3: 3345
• 3a Evans PA, Baikstis T, Inglesby PA. Tetrahedron 2013; 69: 7826
• 3b Shareef A.-R, Sherman DH, Montgomery J. Chem. Sci. 2012; 3: 892
• 3c Stolley RM, Duong HA, Thomas DR, Louie J. J. Am. Chem. Soc. 2012; 134: 15154
• 3d Hyster TK, Rovis T. Chem. Sci. 2011; 2: 1606
• 3e Sun Z.-M, Chen S.-P, Zhao P. Chem. Eur. J. 2010; 16: 2619
• 3f Trenkle JD, Jamison TF. Angew. Chem. Int. Ed. 2009; 48: 5366
• 3g Nakao Y, Kanyiva KS, Hiyama T. J. Am. Chem. Soc. 2008; 130: 2448
• 3h Shimizu K, Takimoto M, Mori M. Org. Lett. 2003; 5: 2323
• 3i Cámpora J, Palma P, Carmona E. Coord. Chem. Rev. 1999; 193: 208
• 4a Kimura M, Ezoe A, Mori M, Tamaru Y. J. Am. Chem. Soc. 2005; 127: 201
• 4b Kojima K, Kimura M, Tamaru Y. Chem. Commun. 2005; 4717
• 4c Ezoe A, Kimura M, Inoue T, Mori M, Tamaru Y. Angew. Chem. Int. Ed. 2002; 41: 2784
• 5a Kimura M, Togawa M, Tatsuyama Y, Matsufuji K. Tetrahedron Lett. 2009; 50: 3982
• 5b Kimura M, Kojima K, Tatsuyama Y, Tamaru Y. J. Am. Chem. Soc. 2006; 128: 6332
• 6 Mori Y, Onodera G, Kimura M. Chem. Lett. 2014; 43: 97
• 7 See the Supporting Information.
• 8a Wilke G. Angew. Chem., Int. Ed. Engl. 1988; 27: 185
• 8b Baker R, Crimmin MJ. J. Chem. Soc., Perkin Trans. 1 1979; 1264
• 8c Akutagawa S. Bull. Chem. Soc. Jpn. 1976; 49: 3646
• 8d Baker R. Chem. Rev. 1973; 73: 487
• 9a Terao J, Oda A, Ikumi A, Nakamura A, Kuniyasu H, Kambe N. Angew. Chem. Int. Ed. 2003; 42: 3412
• 9b Takimoto M, Mori M. J. Am. Chem. Soc. 2002; 124: 10008
• 9c Benn R, Büssemeier B, Holle S, Jolly PW, Mynott R, Tkatchenko I, Wilke G. J. Organomet. Chem. 1985; 279: 63