Copper‐Catalyzed Stereoselective Defluorinative Borylation and Silylation of gem‐Difluoroalkenes

The copper‐catalyzed stereoselective defluorinative borylation and silylation of gem‐difluoroalkenes was developed. The protocol led to the exclusive formation of Z type monofluoroalkenyl borons and silanes in generally good efficiency with broad substrate scope. The products formed could be readily...

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Published inAdvanced synthesis & catalysis Vol. 360; no. 5; pp. 1032 - 1037
Main Authors Tan, Dong‐Hang, Lin, E, Ji, Wei‐Wei, Zeng, Yao‐Fu, Fan, Wen‐Xin, Li, Qingjiang, Gao, Hui, Wang, Honggen
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.03.2018
Wiley Subscription Services, Inc
Subjects
borylation
Chemical bonds
Chemistry
Chemistry, Applied
Chemistry, Organic
Copper
defluorinative
gem-difluoroalkene
Physical Sciences
Science & Technology
Silanes
silylation
Substrates
KETONE N-TOSYLHYDRAZONES
defluorinative
ENANTIOSELECTIVE SYNTHESIS
P-QUINONE METHIDES
BUILDING-BLOCKS
borylation
HALOGENATING AGENTS
C-F ACTIVATION
HYDROCARBON ANALOGS
H BOND ACTIVATION
gem-difluoroalkene
silylation
FACILE ACCESS
copper
GRIGNARD-REAGENTS
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Summary:The copper‐catalyzed stereoselective defluorinative borylation and silylation of gem‐difluoroalkenes was developed. The protocol led to the exclusive formation of Z type monofluoroalkenyl borons and silanes in generally good efficiency with broad substrate scope. The products formed could be readily transformed to other F‐containing molecules by taking advantage of the versatile reactivities of C−B and C−Si bonds. Experimental and theoretical mechanistic studies were conducted which support an olefin insertion/syn‐planar β‐F elimination pathway.
Bibliography:These authors contributed equally.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201701497