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Recyclable and reusable NiCl 2 (PPh 3 ) 2 /CuI/PEG‐400/H 2 O system for the sonogashira coupling reaction of aryl iodides with alkynes
Author(s) -
Wei Ting,
Zhang Tingli,
Huang Bin,
Tuo Yuxin,
Cai Mingzhong
Publication year - 2015
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3394
Subject(s) - sonogashira coupling , chemistry , aryl , catalysis , ethylene glycol , peg 400 , peg ratio , medicinal chemistry , combinatorial chemistry , organic chemistry , polymer chemistry , palladium , alkyl , polyethylene glycol , finance , economics
A stable and highly efficient NiCl2(PPh 3 ) 2 /CuI/PEG‐400/H 2 O catalytic system for the Sonogashira reaction has been developed. In the presence of NiCl 2 (PPh 3 ) 2 and CuI, the coupling reaction of aryl iodides with terminal alkynes was carried out smoothly in a mixture of poly(ethylene glycol) (PEG‐400) and water at 100°C with K 2 CO 3 as base to afford a variety of arylacetylenes in good to excellent yields. The isolation of the products was readily performed by extraction with petroleum ether, and the NiCl 2 (PPh 3 ) 2 /CuI/PEG‐400/H 2 O system could be easily recycled and reused six times without significant loss of catalytic activity . Our system not only avoids the use of easily volatile organic solvents but also solves the basic problem of catalyst reuse. Copyright © 2015 John Wiley & Sons, Ltd.