Premium
Base‐Mediated Radical Borylation of Alkyl Sulfones
Author(s) -
Huang Mingming,
Hu Jiefeng,
Krummenacher Ivo,
Friedrich Alexandra,
Braunschweig Holger,
Westcott Stephen A.,
Radius Udo,
Marder Todd B.
Publication year - 2022
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202103866
Subject(s) - borylation , alkyl , base (topology) , chemistry , organic chemistry , mathematics , aryl , mathematical analysis
A practical and direct method was developed for the production of versatile alkyl boronate esters via transition metal‐free borylation of primary and secondary alkyl sulfones. The key to the success of the strategy is the use of bis(neopentyl glycolato) diboron (B 2 neop 2 ), with a stoichiometric amount of base as a promoter. The practicality and industrial potential of this protocol are highlighted by its wide functional group tolerance, the late‐stage modification of complex compounds, no need for further transesterification, and operational simplicity. Radical clock, radical trap experiments, and EPR studies were conducted which show that the borylation process involves radical intermediates.