Hydrotrifluoroacetylation of Alkenes via Designer Masked Acyl Reagents

Because of its impressive ability to promote pharmaceutical activity, the introduction of trifluoromethylacyl (CF3CO) functionality into organic compounds has become an important and growing research area. Although various protocols have been developed to access trifluoroketones, the use of trifluor...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2023-05, Vol.145 (21), p.11530-11536
Main Authors: Han, Sangil, Samony, Kyra L., Nabi, Rifat N., Bache, Campbell A., Kim, Daniel K.
Format: Article
Language:English
Subjects:
alkenes
Lewis acids
Lewis bases
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:Because of its impressive ability to promote pharmaceutical activity, the introduction of trifluoromethylacyl (CF3CO) functionality into organic compounds has become an important and growing research area. Although various protocols have been developed to access trifluoroketones, the use of trifluoroacetyl radicals remains virtually undeveloped. Herein, we disclose a novel method for trifluoroacetylation through an umpolung reagent, thereby transforming an electrophilic radical into a nucleophilic radical. The applicability of this transformation is highlighted by large-scale, late-stage reactions of complex bioactive molecules sclareolide and loratadine. Furthermore, the direct transformation of trifluoromethyl ketones into various fluorinated analogues illustrates the potential synthetic application of our developed method.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.3c04294