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Cyclization Strategies to Polyenes Using Pd(II)-Catalyzed Couplings of Pinacol Vinylboronates

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journal contribution
posted on 2012-08-17, 00:00 authored by Robert G. Iafe, Daniel G. Chan, Jonathan L. Kuo, Byron A. Boon, Darius J. Faizi, Tomomi Saga, Jonathan W. Turner, Craig A. Merlic
As a complement to Pd(0)-catalyzed cyclizations, seven Pd(II)-catalyzed cyclization strategies are reported. α,ω-Diynes are selectively hydroborated to bis(boronate esters), which cyclize under Pd(II)-catalysis producing a diverse array of small, medium, and macrocyclic polyenes with controlled E,E, Z,Z, or E,Z stereochemistry. Various functional groups are tolerated including aryl bromides, and applications are illustrated.