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Synthesis 2023; 55(15): 2285-2303
DOI: 10.1055/a-2017-4868
DOI: 10.1055/a-2017-4868
short review
Special Issue dedicated to Prof. David A. Evans
Recent Developments of Palladium- and Rhodium-Catalyzed β-Carbon Elimination Strategies
We thank the University of Toronto (UofT), the Natural Science and Engineering Research Council (NSERC), Alphora Research Inc. and Kennarshore Inc. for financial support. A.D.M thanks NSERC for an NSERC Vanier fellowship. B. M. thanks NSERC for a CGS D fellowship.
Abstract
The activation of C–C bonds via transition metal catalysis has become an increasingly popular strategy in organic synthesis. An emerging method to cleave C–C bonds is to facilitate a β-carbon elimination using rhodium or palladium catalysis. This elementary step typically relies on a thermodynamic driving force, such as the relief of ring strain or steric strain. More recently, the use of neopentyl metal species or chelation assistance has enabled this difficult transformation. This review will cover recent synthetic applications of β-carbon eliminations under palladium and rhodium catalysis.
1 Introduction
2 Chelation-Assisted β-Carbon Elimination Reactions
3 β-Carbon Elimination from Neopentyl–Pd Species
4 Pd-Catalyzed Catellani Reactions
5 β-Carbon Elimination Reactions of Cyclopropanes
6 Conclusion
Publication History
Received: 11 November 2022
Accepted after revision: 22 January 2023
Accepted Manuscript online:
22 January 2023
Article published online:
16 March 2023
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