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Palladium-Catalyzed Cross-Coupling Reaction of Heteroaryltriolborates with Aryl Halides for Synthesis of Biaryls
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)
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Submitter: 山本 靖典
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