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

被引:60
作者
Cai, Zhong-Jian [1 ]
Liu, Chen-Xu [1 ]
Wang, Qiang [1 ]
Gu, Qing [1 ]
You, Shu-Li [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
PLANAR CHIRAL FERROCENES; ASYMMETRIC-SYNTHESIS; C(SP(3))-H BONDS; HIGHLY EFFICIENT; AMINO-ACIDS; ACTIVATION; FUNCTIONALIZATION; C(SP(2))-H; CONSTRUCTION; CYCLIZATION;
D O I
10.1038/s41467-019-12181-x
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
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.
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页数:8
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