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Updated: Jun 4, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Pd-Catalyzed Migratory 1,1-Cycloannulation Reaction of Alkenes
Jin-Ping Wang1,2, Tao Liu1, Yichen Wu1
1State Key Laboratory of Organometallic Chemistry and Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS 345 Lingling Road, Shanghai 200032, P. R. China.
Abstract:
Here, we report a novel strategy for the preparation of diverse heterocycles via a Pd-catalyzed migratory 1,1-cycloannulation reaction (MCAR) of alkenes. Starting from readily available alkenyl amines and alkenyl alcohols, this approach allows the formation of a wide range of five- to seven-membered azaheterocycles and oxaheterocycles with high efficiency and good functional group tolerance. The key to the realization of this reaction is the use of 4-iodophenol or 2-iodophenol derivatives where the phenolic hydroxyl group plays a critical role in controlling the direction of migration and the ring-size of the heterocycles through the formation of a quinone methide intermediate.
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