Work

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

Year: 2026

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.6c01598

Authors: Marco Di Matteo, Tullio Crovetto, Luis F. Veiros, Giovanni Poli, Alexandre Pradal

Institutions: Centre National de la Recherche Scientifique, Sorbonne Université, University of Lisbon, Instituto Superior Técnico

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

OpenAlex ID: W7160529007

FWCI:

Cites: 44

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Related to: 10