Thioketone-directed rhodium(I) catalyzed enantioselective C-H bond arylation of ferrocenes

Zhong-Jian Cai, Chen-Xu Liu, Qiang Wang, Qing Gu () and Shu-Li You ()
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Zhong-Jian Cai: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
Chen-Xu Liu: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
Qiang Wang: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
Qing Gu: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
Shu-Li You: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

Nature Communications, 2019, vol. 10, issue 1, 1-8

Abstract: Abstract Planar chiral ferrocenes have received great attention in both academia and industry. Although remarkable progresses have been made over the past decade, the development of efficient and straightforward methods for the synthesis of enantiopure planar chiral ferrocenes remains highly challenging. Herein, we report a rhodium(I)/phosphonite catalyzed thioketone-directed enantioselective C-H bond arylation of ferrocenes. Readily available aryl iodides are used as the coupling partners in this transformation, leading to a series of planar chiral ferrocenes in good yields and excellent enantioselectivities (up to 86% yield, 99% ee). Of particular note, heteroaryl coupled ferrocenes, which are difficult to access with previous approaches, can be obtained in satisfactory results.

Date: 2019
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DOI: 10.1038/s41467-019-12181-x

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