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1.2 Intramolecular Heck Reactions

DOI: 10.1055/sos-SD-221-00020

Jammi, S.; Nottingham, C.; Guiry, P. J.Science of Synthesis: Metal-Catalyzed Cyclization Reactions, (2016155.

General Introduction

The vinylation of aryl/vinyl/alkyl halides or pseudohalides catalyzed by palladium(0), the Heck cross-coupling reaction, has developed into one of the most widely employed C—C bond-forming reactions in organic synthesis since its discovery in 1968 by Heck.[‌1‌‌3‌] The intramolecular version of this reaction was first realized by Mori and co-workers in 1977 through the formation of indole 1 (Scheme 1).[‌4‌] Since then the intramolecular Heck reaction has been extensively utilized in the construction of isolated, fused, bridged, or spiro rings of various sizes and as a key step in the total synthesis of many natural products.[‌5‌] Its application in cascade/domino processes has further increased the usefulness of the reaction in multiple bond formation to construct cyclic or polycyclic systems in both asymmetric and nonasymmetric modes. Additionally, tertiary or quaternary stereocenters can be established using the asymmetric intramolecular Heck reaction.[‌6‌‌8‌]

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