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Synthesis of gem ‐Difluorocyclopropa(e)nes and O ‐ , S ‐ , N ‐ , and P‐Difluoromethylated Compounds with TMSCF 2 Br
Author(s) -
Li Lingchun,
Wang Fei,
Ni Chuanfa,
Hu Jinbo
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201306703
Subject(s) - difluorocarbene , phosphine , chemistry , medicinal chemistry , bromide , cycloaddition , hydroxide , aqueous solution , phenols , organic chemistry , catalysis
Two‐in‐one: Me 3 SiCF 2 Br is an efficient difluorocarbene source and is compatible with both neutral and aqueous basic conditions. Bromide‐ion‐initiated [2+1] cycloaddition with alkenes/alkynes and hydroxide ion promoted α‐addition with (thio)phenols, (thio)alcohols, sulfinates, heterocyclic amines, and H‐phosphine oxides give the corresponding gem ‐difluorinated compounds with broad functional‐group tolerance.