Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 3, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103866
Keywords
boron; boronate; boronic acid; metal-free; radical
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Funding
- Julius-Maximilians-Universitat Wurzburg
- China Scholarship Council (CSC)
- Alexander von Humboldt Foundation
- National Natural Science Foundation of China [21901114]
- Natural Science Foundation of Jiangsu Province [BK20180685]
- Projekt DEAL
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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 method shows great potential in industrial application with its wide functional group tolerance and operational simplicity.
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.
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