Construction of Axial Chirality by Rhodium-Catalyzed Asymmetric Dehydrogenative Heck Coupling of Biaryl Compounds with Alkenes†
Jun Zheng
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Search for more papers by this authorCorresponding Author
Prof. Dr. Shu-Li You
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/Search for more papers by this authorJun Zheng
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Search for more papers by this authorCorresponding Author
Prof. Dr. Shu-Li You
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/Search for more papers by this authorWe thank the National Basic Research Program of China (973 Program 2015CB856600) and the National Natural Science Foundation of China (21025209, 21121062, and 21332009) for generous financial support.
Graphical Abstract
An axe to grind? Novel axially chiral biaryls were synthesized by the direct CH bond olefination of biaryl compounds, using a chiral [Cp*RhIII] catalyst (1), in good to excellent yields and enantioselectivities. The biaryls were found as suitable ligands for rhodium-catalyzed asymmetric conjugate addition reactions.
Abstract
Enantioselective construction of axially chiral biaryls by direct CH bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct CH bond olefination of biaryl compounds, using a chiral [Cp*RhIII] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium-catalyzed asymmetric conjugate additions.
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