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Synthesis of Functionalized o ‐, m ‐, and p ‐Terphenyl Derivatives by Consecutive Cross‐Coupling Reactions of Triazene‐Substituted Arylboronic Esters
Author(s) -
Liu ChingYuan,
Gavryushin Andrey,
Knochel Paul
Publication year - 2007
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200700099
Subject(s) - triazene , terphenyl , chemistry , aryl , bifunctional , coupling reaction , negishi coupling , palladium , halide , organic chemistry , medicinal chemistry , polymer chemistry , reagent , combinatorial chemistry , catalysis , alkyl
Triazene‐substituted arylboronic esters were prepared readily from the corresponding aryl magnesium derivatives and shown to function as a new class of donor–acceptor‐substituted coupling reagents. The selective functionalization of these aromatic derivatives led to a wide variety of terphenyl derivatives in which the original bifunctional unit (often further substituted with another functional group) formed the central aromatic ring. The functionalized terphenyl derivatives were formed in two efficient cross‐coupling steps from the triazene‐substituted boronic esters: Suzuki cross‐coupling with an aryl halide was followed by BF 3 ⋅OEt 2 ‐induced palladium‐catalyzed coupling of the diazonium salt generated in situ from the triazene with an arylboronic acid.