Abstract
An efficient, transition-metal free, and practical approach to cis-bis(boryl)alkenes from various alkynes was disclosed in the presence of a catalytic amount of K2CO3 under mild conditions. Meanwhile, tetrasubstituted alkenes and phenanthrene derivatives were readily constructed from the target diborylalkenes via Suzuki-Miyaura cross coupling.
References
(a) Meier H. Angew Chem Int Ed Engl, 1992, 31: 1399–1420
Lo SC, Burn PL. Chem Rev, 2007, 107: 1097–1116
Neeve EC, Geier SJ, Mkhalid IAI, Westcott SA, Marder TB. Chem Rev, 2016, 116: 9091–9161
Cuenca AB, Shishido R, Ito H, Fernández E. Chem Soc Rev, 2017, 46: 415–430
(a) Roupe K, Remsberg C, Yanez J, Davies N. Curr Clin Pharm, 2006, 1: 81–101
Cottart CH, Nivet-Antoine V, Beaudeux JL. Mol Nutr Food Res, 2014, 58: 7–21
Wang C, Wu C, Ge S. ACS Catal, 2016, 6: 7585–7589
Xu L, Zhang S, Li P. Chem Soc Rev, 2015, 44: 8848–8858
(a) Flynn AB, Ogilvie WW. Chem Rev, 2007, 107: 4698–4745
Hata T, Kitagawa H, Masai H, Kurahashi T, Shimizu M, Hiyama T. Angew Chem Int Ed, 2001, 40: 790–792
(a) Faggi E, Sebastian RM, Pleixats R, Vallribera A, Shafir A, Rodriguez-Gimeno A, Ramirez de Arellano C. J Am Chem Soc, 2010, 132: 17980–17982
Shimizu M, Nagao I, Tomioka Y, Hiyama T. Angew Chem Int Ed, 2008, 47: 8096–8099
Shimizu M, Nagao I, Tomioka Y, Kadowaki T, Hiyama T. Tetrahedron, 2011, 67: 8014–8026
Yoshida H, Kawashima S, Takemoto Y, Okada K, Ohshita J, Takaki K. Angew Chem Int Ed, 2012, 51: 235–238
(a) Lee CI, Shih WC, Zhou J, Reibenspies JH, Ozerov OV. Angew Chem Int Ed, 2015, 54: 14003–14007
Iwadate N, Suginome M. J Am Chem Soc, 2010, 132: 2548–2549
(a) Baker RT, Nguyen P, Marder TB, Westcott SA. Angew Chem Int Ed Engl, 1995, 34: 1336–1338
Ramírez J, Sanaú M, Fernández E. Angew Chem Int Ed, 2008, 47: 5194–5197
Chen Q, Zhao J, Ishikawa Y, Asao N, Yamamoto Y, Jin T. Org Lett, 2013, 15: 5766–5769
Nakagawa N, Hatakeyama T, Nakamura M. Chem Eur J, 2015, 21: 4257–4261
(a) Ishiyama T, Matsuda N, Miyaura N, Suzuki A. J Am Chem Soc, 1993, 115: 11018–11019
Ishiyama T, Matsuda N, Murata M, Ozawa F, Suzuki A, Miyaura N. Organometallics, 1996, 15: 713–720
Lesley G, Nguyen P, Taylor NJ, Marder TB, Scott AJ, Clegg W, Norman NC. Organometallics, 1996, 15: 5137–5154
Thomas RL, Souza FES, Marder TB. J Chem Soc Dalton Trans, 2001, 30: 1650–1656
Burks HE, Kliman LT, Morken JP. J Am Chem Soc, 2009, 131: 9134–9135
Alonso F, Moglie Y, Pastor-Pérez L, Sepúlveda-Escribano A. ChemCatChem, 2014, 6: 857–865
(a) Adams CJ, Baber RA, Batsanov AS, Bramham G, Charmant JPH, Haddow MF, Howard JAK, Lam WH, Lin Z, Marder TB, Norman NC, Orpen AG. Dalton Trans, 2006, 248: 1370–1373
Yang Z, Cao T, Han Y, Lin W, Liu Q, Tang Y, Zhai Y, Jia M, Zhang W, Zhu T, Ma S. Chin J Chem, 2017, 35: 1251–1262
Ansell MB, Menezes da Silva VH, Heerdt G, Braga AAC, Spencer J, Navarro O. Catal Sci Technol, 2016, 6: 7461–7467
(a) Bonet A, Pubill-Ulldemolins C, Bo C, Gulyás H, Fernández E. Angew Chem Int Ed, 2011, 50: 7158–7161
Miralles N, Cid J, Cuenca AB, Carbó JJ, Fernández E. Chem Commun, 2015, 51: 1693–1696
Cuenca AB, Zigon N, Duplan V, Hoshino M, Fujita M, Fernández E. Chem Eur J, 2016, 22: 4723–4726
Bonet A, Sole C, Gulyás H, Fernández E. Org Biomol Chem, 2012, 10: 6621–6623e
Blaisdell TP, Caya TC, Zhang L, Sanz-Marco A, Morken JP. J Am Chem Soc, 2014, 136: 9264–9267
Miralles N, Alam R, Szabó KJ, Fernández E. Angew Chem Int Ed, 2016, 55: 4303–4307
Deng CM, Ma YF, Wen YM. ChemistrySelect, 2018, 3: 1202–1204
(a) Nagao K, Ohmiya H, Sawamura M. Org Lett, 2015, 17: 1304–1307
Yoshimura A, Takamachi Y, Han LB, Ogawa A. Chem Eur J, 2015, 21: 13930–13933
Yoshimura A, Takamachi Y, Mihara K, Saeki T, Kawaguchi S, Han LB, Nomoto A, Ogawa A. Tetrahedron, 2016, 72: 7832–7838
(a) Nagashima Y, Hirano K, Takita R, Uchiyama M. J Am Chem Soc, 2014, 136: 8532–8535
Kojima C, Lee KH, Lin Z, Yamashita M. J Am Chem Soc, 2016, 138: 6662–6669
Verma A, Snead RF, Dai Y, Slebodnick C, Yang Y, Yu H, Yao F, Santos WL. Angew Chem Int Ed, 2017, 56: 5111–5115
(a) Feng Q, Yang K, Song Q. Chem Commun, 2015, 51: 15394–15397
Ding W, Song Q. Org Chem Front, 2016, 3: 14–18
Kuang Z, Li B, Song Q. Chem Commun, 2018, 54: 34–37
Xuan Q, Kong W, Song Q. J Org Chem, 2017, 82: 7602–7607
Gao G, Yan J, Yang K, Chen F, Song Q. Green Chem, 2017, 19: 3997–4001
Yang K, Song Q. Green Chem, 2016, 18: 932–936
Gao G, Kuang Z, Song Q. Org Chem Front, 2018, 5: 2249–2253
Tong S, Xu Z, Mamboury M, Wang Q, Zhu J. Angew Chem Int Ed, 2015, 54: 11809–11812
The substrate material was synthesized with Ref. [5]
Acknowledgements
This work was supported by the National Natural Science Foundation (21772046), Program of Innovative Research Team of Huaqiao University (Z14X0047), the Recruitment Program of Global Experts (1000 Talents Plan), the Natural Science Foundation of Fujian Province (2016J01064) and Postgraduates’ Innovative Fund in Scientific Research of Huaqiao University for K. Z. We also thank Instrumental Analysis Center of Huaqiao University.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Kuang, Z., Gao, G. & Song, Q. Base-catalyzed diborylation of alkynes: synthesis and applications of cis-1,2-bis(boryl)alkenes. Sci. China Chem. 62, 62–66 (2019). https://doi.org/10.1007/s11426-018-9344-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-018-9344-4