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Intramolecular Catalyst Transfer over Sterically Hindered Arenes in Suzuki Cross‐Coupling Reactions
Author(s) -
Zhu YuXing,
Li EnCi,
Shen Kang,
Hang Xiaochun,
Bonnesen Peter V.,
Hong Kunlun,
Zhang HongHai,
Huang Wei
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900228
Subject(s) - chemistry , intramolecular force , steric effects , suzuki reaction , phenylboronic acid , catalysis , coupling reaction , photochemistry , combinatorial chemistry , polymer chemistry , organic chemistry , medicinal chemistry , palladium
The intramolecular catalyst transfer over sterically hindered arenes in Suzuki cross‐coupling reaction was investigated by the reaction of ortho ‐substituted dibromoarenes with equimolar ortho ‐substituted phenylboronic acid in the presence of NHC based PEPPSI‐IPr as catalyst. The diarylarene species of the form Ar’−Ar−Ar’ were observed as major product, which suggested the intramolecular transfer of Pd(0) over sterically hindered arenes proceeded smoothly in Suzuki cross‐coupling reaction. Furthermore, our studies also demonstrated that intramolecular catalyst transfer could be a useful tool to improve the polymerization efficiency, especially in the synthesis of ortho ‐linked polyarenes.