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Synlett 2022; 33(08): 705-712
DOI: 10.1055/s-0041-1737325
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How Rhodium(I)-Catalyzed Phosphorus(III)-Directed C–H Bond Functionalizations Can Improve the Catalytic Activities of Phosphines

Zhuan Zhang
b   Guangxi Key Laboratory of Electrochemical Energy Materials, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, P. R. of China
,
Natacha Durand
a   Univ Rennes, CNRS, UMR6226, F-3500 Rennes, France
,
Jean-François Soulé  ∗
a   Univ Rennes, CNRS, UMR6226, F-3500 Rennes, France
› Author AffiliationsWe thank the CNRS, UR1, Agence Nationale de la Recherche (Grant No. ANR-20-CE07-0019-01) for providing financial support, and Z.Z. thanks the China Scholarship Council (CSC) for his Ph.D. grant (Grant No. 201706780007).
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Abstract

Trivalent-phosphorus-containing molecules are widely used in fields ranging from catalysis to materials science. Efficient catalytic methods for their modifications, providing straightforward access to novel hybrid structures with superior catalytic activities, are highly desired to facilitate reaction improvement or discovery. We have recently developed new methods for synthesizing polyfunctional phosphines by C–C cross-couplings through rhodium-catalyzed C–H bond activation. These methods use a native P(III) atom as a directing group, and can be used in regioselective late-stage functionalization of phosphine ligands. Interestingly, some of the modified phosphines outperform their parents in Pd-catalyzed cross-coupling reactions.

1 Introduction

2 Early Examples of Transition-Metal-Catalyzed P(III)-Directed C–H Bond Activation/Functionalizations

3 Synthesis of Polyfunctional Biarylphosphines by Late-Stage Alkylation: Application in Carboxylation Reactions

4 Synthesis of Polyfunctional Biarylphosphines by Late-Stage Alkenylation: Application in Amidation Reactions

5 Conclusion

Keywords

phosphines - C–H bond activation - late-stage functionalization - rhodium catalysis - CO2 fixation - ligands


Publication History

Received: 14 October 2021

Accepted after revision: 30 November 2021

Article published online:
10 January 2022

© 2022. Thieme. All rights reserved

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