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

27 February 2019, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

Nickel
transmetalation
fluorine
fluoroalkyl

Supplementary materials

Title
Description
Actions
Title
Huang Shen SI 0221
Description
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Version History

Feb 27, 2019 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.7773611.v1
D O I: 10.26434/chemrxiv.7773611.v1 [opens in a new tab]

Funding

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

Author’s competing interest statement

No conflict of interest

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