Direct Nucleophilic Difluoromethylation of Carbonyl Compounds

被引：60

作者：

Deng, Zuyong

Lin, Jin-Hong

Cai, Ji

Xiao, Ji-Chang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 13期

关键词：

QUATERNARY PHOSPHONIUM HYDROXIDES; COPPER-MEDIATED DIFLUOROMETHYLATION; GEM-DIFLUOROOLEFINATION; SUBSTITUTION-REACTIONS; WITTIG REACTION; SALTS; DECOMPOSITION; ALDEHYDES; IODIDES; REAGENT;

D O I：

10.1021/acs.orglett.6b01425

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phosphonium salt ([Ph3P+CF2H] Br-, DFPB) was found to be an efficient nucleophilic difluoromethylation reagent. Although DFPB is known as a phosphonium ylide precursor, its reaction with carbonyl compounds under traditional "Wittig reaction conditions" did not give the expected Wittig difluoroolefinated products, but afforded the nucleophilic difluoromethylation products, alpha-CF2H alcohols. Mechanistic investigation reveals that the unexpected transformation proceeded via the direct transfer of the CF2H group, which resulted from the high P-O affinity.

引用

页码：3206 / 3209

页数：4

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