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A Phosphane‐Free, Atom‐Efficient Cross‐Coupling Reaction of Triarylbismuths with Acyl Chlorides Catalyzed by MCM‐41‐Immobilized Palladium Complex
Author(s) -
Zhao Hong,
Yin Lin,
Cai Mingzhong
Publication year - 2013
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.201201432
Subject(s) - chemistry , palladium , catalysis , denticity , yield (engineering) , heterogeneous catalysis , coupling reaction , filtration (mathematics) , base (topology) , mcm 41 , combinatorial chemistry , organic chemistry , polymer chemistry , mesoporous material , crystal structure , mathematical analysis , materials science , statistics , mathematics , metallurgy
The first phosphane‐free, heterogeneous, atom‐efficient cross‐coupling reaction of triarylbismuths and acyl chlorides was achieved in N ‐methylpyrrolidone (NMP) with Bu 3 N as the base at 80 °C in the presence of 1.5 mol‐% MCM‐41‐immobilized bidentate nitrogen palladium complex [MCM‐41–2N‐Pd(OAc) 2 , MCM = mobile crystalline material] to yield a variety of unsymmetrical biaryl ketones in good to excellent yields. This heterogeneous palladium catalyst exhibited a high activity, which was similar to that of Pd(PPh 3 ) 4 . The catalyst can be recovered by a simple filtration of the reaction solution and recycled in at least 10 consecutive trials without any decrease in activity. Our system not only avoids the use of phosphane ligands, but also solves the basic problem of palladium catalyst recovery and reuse.