Palladium-Catalyzed Intermolecular Ditrifluoromethoxylation of Unactivated Alkenes: CF3O‑Palladation Initiated by Pd(IV)

A novel palladium-catalyzed intermolecular ditrifluoromethoxylation of unactivated alkenes has been developed, using a new electrophilic reagent, SelectfluorCN, as a strong oxidant, and AgOCF3 as a trifluoromethoxide source. Preliminary mechanistic studies revealed that the reaction was possibly ini...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2018-01, Vol.140 (4), p.1207-1210
Main Authors: Chen, Chaohuang, Luo, Yixin, Fu, Liang, Chen, Pinhong, Lan, Yu, Liu, Guosheng
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A novel palladium-catalyzed intermolecular ditrifluoromethoxylation of unactivated alkenes has been developed, using a new electrophilic reagent, SelectfluorCN, as a strong oxidant, and AgOCF3 as a trifluoromethoxide source. Preliminary mechanistic studies revealed that the reaction was possibly initiated by Pd­(IV) species, and an unusual cis-addition of CF3O–Pd­(IV) into the double bond leads to the formation of the first C–OCF3 bond; in addition, the second C–OCF3 bond was produced through reductive elimination at high-valent palladium center.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b11470