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Facilitating the Transmetalation Step with Aryl-Zincates in Nickel-Catalyzed Enantioselective Arylation of Secondary Benzylic Halides

preprint
submitted on 27.02.2019 and posted on 27.02.2019 by Weichen Wan, Mei Hu, Xiaolong Wan, Qilong Shen

A method for the highly enantioselective construction of fluoroalkyl-substituted stereogenic center by a nickel-catalyzed asymmetric Suzuki-Miyaura coupling of a-bromobenzyl trifluoro-/difluoro-/monofluoromethanes with a variety of lithium organoborate in the presence of 1.0 equivalent of ZnBr2 was described. Preliminary mechanistic studies disclosed that reaction of lithium organoborate with ZnBr2 generated a zincate [Ph2ZnBr]Li, which facilitates the transmetallation step of the nickel-catalyzed cross-coupling reaction to enable high enantioselectivity.

Funding

National Natural Science Foundation of China (21625206, 21632009, 21572258, 21421002) and the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB20000000).

History

Email Address of Submitting Author

shenql@sioc.ac.cn

Institution

Shanghai Institute of Organic Chemistry

Country

China

ORCID For Submitting Author

0000-0001-5622-153X

Declaration of Conflict of Interest

No conflict of interest

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