47.1.2.1.5 Synthesis of Alkenes by Cross-Coupling and Heck Reactions

Abstract

Since their discovery, Heck and cross-coupling reactions have become essential for catalytic alkene synthesis. Selected homogeneous methods for non-aromatic and unactivated alkene synthesis by catalytic alkenylation are reviewed herein (ca. 2008–2020). By using new combinations of ligands, additives, co-catalysts, and transition metals, significant advances and new mechanistic insights have been revealed recently. New strategies for accessing a broader substrate scope, milder reaction conditions, higher functional-group compatibility, and highly stereoselective synthesis are highlighted.

Key words

alkenes - cross-coupling reactions - transition-metal catalysis - alkenylation - stereoselective olefin synthesis - stereodivergent olefin synthesis - enantioselective olefin synthesis - oxidative addition - transmetalation - alkene insertion - reductive elimination - Heck reaction - Suzuki–Miyaura coupling - Corriu–Kumada–Tamao coupling - Kosugi–Migita–Stille coupling - Hiyama coupling

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