Sorbates from 1,1-Dialkylsubstituted Alkenes and 3-Haloacrylic Esters via Pd(II)-Isohypsic Catalysis: Focus on Terpenes.

Abstract

Limonene and other 1,1-dialkylsubstituted alkenes undergo a regioselective Pd(II)-catalyzed C-H/C-X coupling with (E) and (Z)-3-bromoacrylates affording 4,4-disubstituted sorbate derivatives as mixtures of geometrical isomers (16 examples). This coupling, unknown to date for the synthesis of 1,3-dienes, follows a mechanism distinct from the well-known Mizoroki-Heck, and works where the Mizoroki-Heck fails. Density functional theory (DFT) computations allowed to propose a plausible mechanism for this transformation.

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