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Updated: Dec 24, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Titanocene-Catalyzed Reductive Domino Epoxide Ring Opening/Defluorinative Cross-Coupling Reaction
Zhiyang Lin1, Yun Lan1, Chuan Wang1,2
1Hefei National Laboratory for Physical Science at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.
Abstract:
Herein, we report a method for efficient synthesis of gem-difluorobishomoallylic alcohols starting from trifluoromethyl-substituted alkenes and epoxides via a titanocene-catalyzed reductive domino reaction, which consists of a Ti(III)-mediated radical-type ring opening and the following allylic defluorinative cross-coupling reaction via sequential radical addition and β-F elimination. Notably, complete regioselectivity and high tolerance of functionalities can be achieved in this reaction. Furthermore, diverse 6-fluoro-3,4-dihydro-2H-pyrans have been prepared through derivatization of the cross-coupling products in one single step.
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