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Heterogeneous Pd/C‐Catalyzed Ligand‐Free, Room‐Temperature Suzuki–Miyaura Coupling Reactions in Aqueous Media
Author(s) -
Maegawa Tomohiro,
Kitamura Yoshiaki,
Sako Satoko,
Udzu Takahiro,
Sakurai Ai,
Tanaka Asami,
Kobayashi Yusuke,
Endo Koichi,
Bora Utpal,
Kurita Takanori,
Kozaki Atsushi,
Monguchi Yasunari,
Sajiki Hironao
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601795
Subject(s) - phenylboronic acid , aryl , chemistry , coupling reaction , catalysis , suzuki reaction , palladium , ligand (biochemistry) , boronic acid , aqueous solution , aqueous medium , combinatorial chemistry , organic chemistry , biochemistry , alkyl , receptor
A mild and efficient ligand‐free Suzuki–Miyaura coupling reaction catalyzed by heterogeneous Pd/C was developed. Aryl bromides and triflates undergo the cross‐coupling with aryl boronic acids in excellent yields without the presence of any additives in aqueous media at room temperature. Aryl vinyl boronic acids are also applicable to this coupling reaction and provide the trans ‐stilbene derivatives in high yields. The application of wet‐type Pd/C to the coupling reaction was achieved without any loss of activity under aerobic conditions, and the reuse of Pd/C is feasible for a fifth run without significant loss of activity. Inductively coupled plasma (ICP) mass‐spectrometric analysis of the filtrate from the reaction mixture of 4‐bromonitrobenzene with phenylboronic acid demonstrated that the palladium metal hardly leached into the solution within the limits of the detector (<1 ppm), thus suggesting that the present Suzuki–Miyaura reaction proceeded by heterogeneous catalysis.