Boron Trihalide Mediated Substitution of Hydroxyl Groups with Alkenyl, Alkynyl, and Allyl Moieties

Abstract

The coupling of alcohols with alkenyl- and alkynylboron dihalides with high olefin stereoselectivity is described. The reaction provides a facile route to internal acetylenes. Notably, the allylation of propargylic alcohols mediated by boron trichloride proceeds smoothly at room temperature and gives excellent regioselectivity.

coupling - boron halide - substitution - Lewis acid

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