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Palladium-Catalyzed Cross-Coupling Reaction of Heteroaryltriolborates with Aryl Halides for Synthesis of Biaryls

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Title: Palladium-Catalyzed Cross-Coupling Reaction of Heteroaryltriolborates with Aryl Halides for Synthesis of Biaryls
Authors: Yamamoto, Yasunori Browse this author
Takizawa, Miho Browse this author
Yu, Xiao-Qiang Browse this author
Miyaura, Norio Browse this author
Keywords: Cross-Coupling Reaction
Organoboron Compound
Heteroaryltriolborate
Ate Complex
Biaryl
Issue Date: 1-Jan-2010
Publisher: Japan Institute of Heterocyclic Chemistry
Journal Title: Heterocycles
Volume: 80
Issue: 1
Start Page: 359
End Page: 368
Publisher DOI: 10.3987/COM-09-S(S)30
Abstract: Cyclic triolborates possessing a heteroaromatic ring on the boron atom [ArB(OCH2)3CHCH3]M (M=K, Na, Li) were prepared in high yields from heteroarylboronic acids, 1,1,1-tris(hydroxymethyl)ethane (triol) and KOH or NaH. The corresponding lithium salts were synthesized from aryllithiums, B(OMe)3 and triol. They were air-stable white solids that were convenient for handling in air. High performance of these triolborates for metal-catalyzed bond-forming reactions was demonstrated in palladium-catalyzed cross-coupling reactions with haloarenes. Although the use of heteroarylboronic acids often results in very low yields due to competitive hydrolytic B-C bond cleavage with water under typical conditions using aqueous bases, triolborates possessing a 2-pyridyl, 3-pyridyl or 2-thiophenyl ring afforded biaryls in high yields at 50-120℃ in anhydrous DMF. There was a strong accelerating effect of CuI for reactions of 2- and 3-pyridylborate derivatives, whereas 2-thiophenyl derivatives reacted smoothly resulting in high yields in the absence of CuI.
Type: article (author version)
URI: http://hdl.handle.net/2115/45016
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: 山本 靖典

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