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Stereospecific Synthesis of ( Z )‐ α ‐Fluoro‐ β ‐trifluoromethyl Vinyl Iodides and Their Application to the Synthesis of Polyfluorinated Thienyl Alkadienes †
Author(s) -
Shen YanChang,
Wang GuoPing
Publication year - 2006
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200690231
Subject(s) - chemistry , trifluoromethyl , substituent , moiety , yield (engineering) , iodide , stannane , stereospecificity , medicinal chemistry , halogenation , organic chemistry , alkyl , catalysis , materials science , metallurgy
The direct iodination of polyfluorinated vinyl stannanes by tin‐iodine exchange methodology was achieved giving( Z )‐ α ‐fluoro‐ β ‐trifluoromethyl vinyl iodides stereospecifically. Changing the substituent in R group from the electron‐withdrawing group to electron‐donating group led to an increase in the yield from 78% to 90%, while it was moved from para to meta position the reaction did not afford a dramatic change in the yield (90% to 95%). In addition, this reaction also can be applied to the vinyl stannane with heterocyclic group. The further coupling reaction of prepared vinyl iodide containing heterocyclic moiety with ( Z )‐ α ‐fluoro‐ β ‐trifluoromethylstannanes gave polyfluorinated heterocyclic alkadienes with 2 E ,4 E ‐selectivity.