Ni- and Pd-Catalyzed Enantioselective 1,2-Dicarbofunctionalization of Alkenes

Abstract

Catalytic enantioselective 1,2-dicarbofunctionalization (1,2-DCF) of alkenes is a powerful transformation of growing importance in organic synthesis for constructing chiral building blocks, bioactive molecules, and agrochemicals. Both in a two- and three-component context, this family of reactions generates densely functionalized, structurally complex products in a single step. Across several distinct mechanistic pathways at play in these transformations with nickel or palladium catalysts, stereocontrol can be obtained through tailored chiral ligands. In this Review we discuss the various strategies, mechanisms, and catalysts that have been applied to achieve enantioinduction in alkene 1,2-DCF.

1 Introduction

2 Two-Component Enantioselective 1,2-DCF via Migratory Insertion

3 Two-Component Enantioselective 1,2-DCF via Radical Capture

4 Three-Component Enantioselective 1,2-DCF via Radical Capture

5 Three-Component Enantioselective 1,2-DCF via Migratory Insertion

6 Miscellaneous Mechanisms

7 Conclusion

Key words

alkenes - cross-coupling - dicarbofunctionalization - enantio­selectivity - nickel - palladium

Publication History

Received: 09 May 2023

Accepted after revision: 12 June 2023

Accepted Manuscript online:
12 June 2023

Article published online:
25 July 2023

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