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gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors
Alternative Title以二氟卡宾试剂TMSCF3或TMSCF2Br对重氮化合物的偕二氟烯化反应: 两种不同卡宾前体在无过渡金属条件下的交叉偶联
Hu MY(胡明友)1; Ni CF(倪传法)1; Li LC(李铃春)1; Han YX(韩永新)1; Hu JB(胡金波)1
2015
Source PublicationJ. Am. Chem. Soc.
Volume137Issue:45Pages:14496-14501
AbstractA 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.
Subtype论文
Subject Area氟化学
DOI10.1021/jacs.5b09888
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000365148500037
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39764
Collection中科院有机氟化学重点实验室
Corresponding AuthorHu JB(胡金波)
Affiliation1.中科院上海有机化学研究所, 有机氟化学重点实验室
2.Merck Research Laboratories
Recommended Citation
GB/T 7714
Hu MY,Ni CF,Li LC,et al. gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors[J]. J. Am. Chem. Soc.,2015,137(45):14496-14501.
APA 胡明友,倪传法,李铃春,韩永新,&胡金波.(2015).gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors.J. Am. Chem. Soc.,137(45),14496-14501.
MLA 胡明友,et al."gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors".J. Am. Chem. Soc. 137.45(2015):14496-14501.
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