Synthesis of Multifunctional α,α-Difluoroketones through Allylic Alkylation of Difluoroenoxysilanes with MBH Carbonates

Bo-Wen Pan; Yang Shi; You-Ping Tian; Ying Zhou; Jian Zhou; Jin-Sheng Yu

doi:10.1002/asia.202001145

Synthesis of Multifunctional α,α-Difluoroketones through Allylic Alkylation of Difluoroenoxysilanes with MBH Carbonates

Chem Asian J. 2020 Dec 1;15(23):4028-4032. doi: 10.1002/asia.202001145. Epub 2020 Nov 4.

Authors

Bo-Wen Pan¹, Yang Shi¹, You-Ping Tian¹, Ying Zhou¹, Jian Zhou^{1

2

3}, Jin-Sheng Yu²

Affiliations

¹ College of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, P. R. China.
² Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, Shanghai, 200062, P. R. China.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai, 200032, P.R. China.

PMID: 33084191
DOI: 10.1002/asia.202001145

Abstract

The first allylic alkylation of difluoroenoxysilanes with MBH carbonates catalyzed by triethylenediamine (DABCO) is developed, which allows rapid access to multifunctional α-gem-difluoroketones with up to 97% yields. Moreover, the gram-scale synthesis and the diversifying transformation of products to valuable gem-difluorinated molecules highlight the practicality of this methodology.

Keywords: Allylic alkylation; MBH carbonates; difluoroenoxysilanes; multifunctional; α-gem-difluoroketones.

Abstract

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