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The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases

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Title: The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases
Authors: Miyaura, N. Browse this author →KAKEN DB
Yanagi, T. Browse this author
Suzuki, A. Browse this author →KAKEN DB
Issue Date: 1981
Publisher: Taylor & Francis Group
Journal Title: Synthetic Communications
Volume: 11
Issue: 7
Start Page: 513
End Page: 519
Publisher DOI: 10.1080/00397918108063618
Abstract: The transition metal-catalyzed reactions of organometallics with organic halides have been extensively studied to prove a new approach to selective formation of carbon-carbon bonds. Recently, such coupling reactions of haloarenes with aryl magnesium1-3 and zinc4 compounds in the presence of palladium or nickel complexes have been reported for the synthesis of biaryls. Davidson and Triggs5 have previously reported that arylboronic acids react with sodium palladate to give the corresponding biaryls in good yields. The synthetic utility of the dimerization reaction is, however, limited because it requires stoichiometric amounts of the palladium compound. On the other hand, we have recently reported that cross-coupling reactions between alkenylboranes and organic halides such as alkenyl,6 alkynyl,6 aryl,7 allyl,8 and benzyl8 halides are effectively catalyzed by a catalytic amount of tetrakis(triphenylphosphine)palladium, Pd(PPh3)4 in the presence of suitable bases as indicated in Scheme 1. Although the detailed mechanistic pathway is not clear at present, the reaction should involve a transmetallation step from alkenylboranes to alkenylpalladiums.
Description: This article is related to the Nobel Prize in chemistry 2010
Rights: This is an electronic version of an article published in Synthetic Communications (1981) 11 (7): 513-519. Synthetic Communications is available online at:
Type: article
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 宮浦 憲夫

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