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Development of a Unique Heterogeneous Palladium Catalyst for the Suzuki–Miyaura Reaction using (Hetero)aryl Chlorides and Chemoselective Hydrogenation
Author(s) -
Ichikawa Tomohiro,
Netsu Moeko,
Mizuno Masahiro,
Mizusaki Tomoteru,
Takagi Yukio,
Sawama Yoshinari,
Monguchi Yasunari,
Sajiki Hironao
Publication year - 2017
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.201700156
Subject(s) - hydrogenolysis , chemistry , catalysis , aryl , palladium , alkyl , organic chemistry , chemoselectivity , combinatorial chemistry
A unique heterogeneous palladium catalyst (7% Pd/WA30) supported on an anion exchange resin, which contains N , N ‐dimethylaminoalkyl functionalities on the polymer backbone, was developed. 7% Pd/WA30 could smoothly catalyze Suzuki–Miyaura reactions of even less reactive heteroaryl chlorides and heteroarylboronic acids to afford various (hetero)biaryls due to the electron‐donating effect of the tert ‐amines on WA30 to Pd species. It was also applicable as a chemoselective hydrogenation catalyst, showing inactivity for the hydrogenolysis of tert ‐butyldimethylsilyl (TBS) ethers, alkyl benzyl ethers, and benzyl alcohols. The tert ‐amines on WA30 acted as moderate catalyst poisons for Pd, resulting in chemoselective hydrogenation. 7% Pd/WA30 was reused for at least five times without any loss of the hydrogenation catalytic activity.