期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 137, 期 45, 页码 14496-14501出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b09888
关键词
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资金
- National Basic Research Program of China [2015CB931900, 2012CB821600]
- National Natural Science Foundation of China [21372246, 21421002, 21472221]
- Shanghai Science and Technology program [15XD1504400]
- MSD China R&D Postdoc Fellowship
- Chinese Academy of Sciences
A new olefination protocol for transition-metal-free cross-coupling of two carbene fragments arising from two different sources, namely, a nonfluorinated carbene fragment resulting from a diazo compound and a difluorocarbene fragment derived from Ruppert-Prakash reagent (TMSCF3) or TMSCF2Br, has been developed. This gem-difluoroolefination proceeds through the direct nucleophilic addition of diazo compounds to difluorocarbene followed by elimination of N-2. Compared to previously reported Cu-catalyzed gem-difluoroolefination of diazo compounds with TMSCF3, which possesses a narrow substrate scope due to a demanding requirement on the reactivity of diazo compounds and in-situ-generated CuCF3, this transition-metal-free protocol affords a general and efficient approach to various disubstituted 1,1-difluoroalkenes, including difluoroacrylates, diaryldifluoroolefins, as well as arylalkyldifluoroolefins. In view of the ready availability of diazo compounds and difluorocarbene reagents and versatile transformations of 1,1-difluoroalkenes, this new gem-difluoroolefination method is expected to find wide applications in organic synthesis.
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