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Selective Green Coupling of Alkynyltins and Allylic Halides to Trienynes via a Tandem Double Stille Reaction
Author(s) -
Meana Isabel,
Albéniz Ana C.,
Espinet Pablo
Publication year - 2010
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.201000430
Subject(s) - allylic rearrangement , chemistry , stille reaction , stereoselectivity , halide , tandem , coupling reaction , palladium , tin , catalysis , reaction conditions , double bond , coupling (piping) , combinatorial chemistry , organic chemistry , metallurgy , materials science , composite material
The palladium‐catalyzed reaction of alkynyltin compounds with allylic chlorides leads to a 2:2 coupling to give trienynes by regio‐ and stereoselective formation of three new CC bonds. The reaction can be applied to different alkynyl and allylic fragments, providing a wide range of trienynes with different substitution patterns in very good yields. They can be prepared in a green way using recyclable polymeric tin alkynyls.