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Nucleophilic Difluoromethylation of Epoxides with PhSO(NTBS)CF 2 H by a Preorganization Strategy
Author(s) -
Shen Xiao,
Liu Qinghe,
Luo Tao,
Hu Jinbo
Publication year - 2014
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.201402506
Subject(s) - nucleophile , regioselectivity , chemistry , ring (chemistry) , epoxide , nucleophilic addition , substrate (aquarium) , combinatorial chemistry , medicinal chemistry , scope (computer science) , organic chemistry , catalysis , computer science , oceanography , programming language , geology
Unlike the facile synthesis of β‐monofluoromethyl alcohols by nucleophilic monofluoromethylation of epoxides, the synthesis of β‐difluoromethyl alcohols by nucleophilic difluoromethylation of epoxides still remains a challenge. Herein, studies on tackling this problem with PhSO(NTBS)CF 2 H ( 2 ; TBS= tert ‐butyldimethylsilyl) are reported. The preorganization of 2 and epoxides with BF 3 ⋅ Et 2 O was found to be crucial for the reaction. The reaction shows excellent regioselectivity and has a broad substrate scope. The facile transformation of the ring‐opened products to β‐difluoromethyl, γ‐difluoromethyl, and β‐difluoromethylenyl alcohols demonstrates the synthetic utility of the reaction.