Cobalt-Catalyzed Regio- and Enantioselective Hydroalkylation of 1,1-Disubstituted Styrenes

Abstract

The metal hydride catalyzed alkene hydroalkylation enables efficient alkyl–alkyl coupling, yielding structurally diverse chiral organic compounds. However, the control of stereochemical selectivity in alkene hydroalkylation still heavily relies on the assistance of substrate Lewis basic functional groups or polar heteroatom functional groups. We have recently developed a cobalt hydride catalytic system and established a paradigm of enantioselective control assisted by C–H···π noncovalent interactions. This approach enables the asymmetric hydroalkylation of 1,1-disubstituted styrenes, thereby circumventing the limitations imposed by substrate heteroatom functional groups.

1 Introduction

2 Reaction Development

3 Synthetic Applications

4 Mechanistic Investigation

5 Conclusion and Future Outlook

Key words

cobalt catalysis - asymmetric catalysis - alkyl–alkyl coupling - alkene hydroalkylation - 1,1-disubstituted styrenes - C–H···π interaction

Publication History

Received: 27 July 2024

Accepted after revision: 02 September 2024

Accepted Manuscript online:
02 September 2024

Article published online:
25 September 2024

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