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Copper‐Catalyzed Hydrodifluoroallylation of Terminal Alkynes to Access ( E )‐1,1‐Difluoro‐1,4‐Dienes
Author(s) -
Wu NuoYi,
Huang Yangen,
Xu XiuHua,
Qing FengLing
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000492
Subject(s) - chemistry , reagent , stereoselectivity , catalysis , copper , hydride , diene , terminal (telecommunication) , organic chemistry , medicinal chemistry , combinatorial chemistry , metal , telecommunications , natural rubber , computer science
A copper‐catalyzed regio‐ and stereoselective hydrodifluoroallylation of terminal alkynes was disclosed. This reaction employs easily available 3‐bromo‐3,3‐difluoropropene (BDFP) as the difluoroallylating reagent and 1,1,3,3‐tetramethyldisiloxane (TMDSO) as the hydride source, affording a variety of ( E )‐1,1‐difluoro‐1,4‐dienes in moderate to good yields. The synthetic utility of this protocol has been demonstrated through the transformation of resulting ( E )‐1,1‐difluoro‐1,4‐diene to difluoromethylated and trifluoromethylated derivatives.