Heterocycles p. 944 - 953 (2016)
Update date:2022-08-31
Topics:
Zhou, Jie
Liu, Xiaohui
Sun, Zhihua
A synthetic method towards chiral benzimidazolium salts is developed. The stereocenter is introduced by direct aromatic substitution of 2-fluoronitrobenzene with optically pure amines. After nitro group reduction, selective arylation of the primary amine is achieved via copper catalyzed Chan-Lam coupling reaction. Finally, cyclization of the diamine with HC(OMe)3 afforded the desired chiral benzimidazolium salts. In situ generated benzimidazole carbenes show potential application for asymmetric catalytic borylation of α,β-unsaturated esters, providing up to 85% ee value with a catalyst loading of only 0.5 mol%.
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