Difluoromethylation of Alkyl Bromides and Iodides with TMSCF 2 H

We describe, for the first time, two protocols for direct difluoromethylation of unactivated alkyl bromides and iodides. Reactions of alkyl iodides with TMSCF H were mediated by a copper catalyst using CsF as the activator, while reactions of less reactive alkyl bromides required a combination of pa...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2021-02, Vol.86 (3), p.2854-2865
Main Authors: Zhao, Haiwei, Lu, Changhui, Herbert, Simon, Zhang, Wei, Shen, Qilong
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We describe, for the first time, two protocols for direct difluoromethylation of unactivated alkyl bromides and iodides. Reactions of alkyl iodides with TMSCF H were mediated by a copper catalyst using CsF as the activator, while reactions of less reactive alkyl bromides required a combination of palladium and a stoichiometric amount of CuI as the catalysts. Preliminary mechanistic studies of the synergistic Pd/Cu-catalyzed difluoromethylation of alkyl bromides suggest that it proceeds likely via a Pd(I)/Pd(III) catalytic cycle.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02783