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Reusable and Ligand‐Free Palladium‐Catalyzed Suzuki‐Miyaura Cross‐Couplings of Aryl Halides with Arylboronic Acids in Tetra ‐n‐ butylammonium Bromide
Author(s) -
XIE YeXiang,
WANG Jian,
LI JinHeng,
LIANG Yun
Publication year - 2008
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200890401
Subject(s) - chemistry , halide , bromide , aryl , tetra , catalysis , palladium , ligand (biochemistry) , aryl halide , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , alkyl , receptor
Ligand‐free and reusable palladium‐catalyzed Suzuki‐Miyaura cross‐coupling reaction performed in TBAB (tetra‐ n ‐butylammonium bromide) was presented. It was found that the amount of water affected these reactions. Excellent results were obtained when there was w =1% of water in TBAB. In the presence of 3 mol% of Pd(OAc) 2 and 1.5 g of TBAB (containing w =1% of water), a number of aryl halides were coupled with arylboronic acids smoothly in moderate to excellent yields. Moreover, the Pd(OAc) 2 /TBAB system among the couplings of aryl bromides and activated chlorides could be recovered and reused three times without a loss of catalytic efficiency.