Deuteriodifluoromethylation and gem‐Difluoroalkenylation of Aldehydes Using ClCF2H in Continuous Flow
Name
2020_AngewChemIntEd.pdf
Description
Accepted version
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2.65 MB
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Adobe PDF
Checksum (MD5)
49f501075a4236b0bfac1cd846858190
Author(s)
Fu, Wai Chung
Jamison, Timothy F
Date Issued
June 2020
Journal
Angewandte Chemie
Publisher
Wiley
Citation
Fu, Wai Chung and Timothy F Jamison."Deuteriodifluoromethylation and gem‐Difluoroalkenylation of Aldehydes Using ClCF2H in Continuous Flow." Angewandte Chemie 132, 33 (June 2020): 13989-13994 © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Version
Author's final manuscript
Abstract
The deuteriodifluoromethyl group (CF₂D) represents a challenging functional group due to difficult deuterium incorporation and unavailability of precursor reagents. Herein, we report the use of chlorodifluoromethane (ClCF₂H) gas in the continuous flow deuteriodifluoromethylation and gem-difluoroalkenylation of aldehydes. Mechanistic studies revealed that the difluorinated oxaphosphetane (OPA) intermediate can proceed via alkaline hydrolysis in the presence of D₂O to provide α-deuteriodifluoromethylated benzyl alcohols or undergo a retro [2+2] cycloaddition under thermal conditions to provide the gem-difluoroalkenylated product.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1002/ange.202004260
