Issue 30, 2020
From the journal:

Chemical Science

Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes†

Feng Shen, ORCID logo a   Long Lu*b  and  Qilong Shen ORCID logo *a  

* Corresponding authors

a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
E-mail: shenql@mail.sioc.ac.cn

b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, China
E-mail: lulong@mail.sioc.ac.cn

Abstract

A transition metal free process for conjunctive functionalization of alkenylboron ate-complexes with electrophilic fluoroalkylthiolating reagents is described, affording β-trifluoroalkylthiolated and difluoroalkylthiolated boronic esters in good yield and excellent diastereoselectivity. The potential applicability of the method was demonstrated by the preparation of a difluoromethylthiolated mimic 12 of a potential drug molecule PF-4191834 for the treatment of asthma.

Graphical abstract: Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes

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Article information

DOI
https://doi.org/10.1039/D0SC03039B
Article type
Edge Article
Submitted
31 May 2020
Accepted
05 Jul 2020
First published
07 Jul 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 8020-8024

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Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes

F. Shen, L. Lu and Q. Shen, Chem. Sci., 2020, 11, 8020 DOI: 10.1039/D0SC03039B

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