In:
Angewandte Chemie International Edition, Wiley, Vol. 57, No. 50 ( 2018-12-10), p. 16544-16548
Abstract:
Organofluorine compounds are widely used in pharmaceutical, agrochemical, and materials sciences. The syntheses and applications of fluorinated organoborons facilitate the rapid and modular assemblies of fluorine‐containing molecules because of the versatility of C−B bonds in diverse chemical transformations. Reported herein is a migratory geminal difluorination of aryl‐substituted alkenyl N ‐methyliminodiacetyl (MIDA) boronates using commercially available Py⋅HF as the fluorine source and hyperiodine as the oxidant. The protocol offers facile access to α‐ and β‐difluorinated alkylboron compounds, both of which have previously been challenging to prepare. Mild reaction conditions, broad substrate scope, good functional‐group tolerance, and moderate to good yields were observed. The utility of these products is demonstrated by further transformations of the C−B bond into other valuable functional groups.
Type of Medium:
Online Resource
ISSN:
1433-7851
,
1521-3773
DOI:
10.1002/anie.201810204
Language:
English
Publisher:
Wiley
Publication Date:
2018
detail.hit.zdb_id:
2011836-3
detail.hit.zdb_id:
123227-7