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Regioselective Synthesis of Tetraalkynylarenes by Consecutive Dual Sonogashira Coupling Reactions of the Bis(triflate) of 4,5‐Diiodobenzene‐1,2‐diol
Author(s) -
Fisher Thomas J.,
Dussault Patrick H.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200079
Subject(s) - chemistry , regioselectivity , sonogashira coupling , trifluoromethanesulfonate , diol , coupling reaction , derivative (finance) , combinatorial chemistry , selectivity , coupling (piping) , stereochemistry , organic chemistry , catalysis , palladium , mechanical engineering , financial economics , engineering , economics
The regioselective synthesis of nonsymmetric tetraalkynylarenes has been readily achieved through consecutive sets of Sonagashira cross‐coupling reactions of the bis(triflate) derivative of 4,5‐diiodobenzene‐1,2‐diol. The initial coupling reactions proceeded with nearly complete selectivity for the reaction at the Ar–I linkages. Subsequent coupling reactions at the Ar–OTf linkages were efficiently conducted. The tetraalkynylarene products are of interest as components of organic molecular materials.