Rhodium-Catalyzed Allylation Reactions

Mahesh Bhagwan Thoke; Qiang Kang

doi:10.1055/s-0037-1611784

Synthesis, Table of Contents

Synthesis 2019; 51(13): 2585-2631
DOI: 10.1055/s-0037-1611784

review

Rhodium-Catalyzed Allylation Reactions

Mahesh Bhagwan Thoke

^aKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, 350002, P. R. of China Email: kangq@fjirsm.ac.cn

^bUniversity of Chinese Academy of Sciences, Beijing, 100049, P. R. of China

,

Qiang Kang *

^aKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, 350002, P. R. of China Email: kangq@fjirsm.ac.cn

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Abstract

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Abstract

Rhodium-catalyzed allylation reactions are well known for their unique selectivity and reactivity due to the high memory effect of Rh as compared to other metals. These reactions involve the substitution of allylic rhodium intermediates with a diverse range of different nucleophiles, leading to C–C and C–heteroatom bond formation. Modern organic chemists are, however, interested in atom-economical protocols under greener pathways and following recent increased understanding of mechanistic aspects of Rh-catalyzed allylation via the hydrofunctionalization of allenes or alkynes, great strides have made in the design and development of new atom-economical protocols. In this article, we review this field from its beginning to current state.

1 Introduction

2 Rhodium-Catalyzed Allylic Substitution

3 Rhodium-Catalyzed Allylation with Allenes

4 Rhodium-Catalyzed Allylation with Alkynes

5 Rhodium-Catalyzed Allylation with Dienes

6 Rhodium-Catalyzed Allylation by ARO of Oxabicyclic Alkenes

7 Rhodium-Catalyzed Enantioselective Allylation in Natural Product and Drug Synthesis

8 Conclusion

Key words

rhodium - allylation - substitution - enantioselective - natural product synthesis

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References

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