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精密有機合成を指向した新しい触媒的ホウ素化反応の開発
Title: | 精密有機合成を指向した新しい触媒的ホウ素化反応の開発 |
Other Titles: | Developments of New Catalytic Borylation Reactions Directed towards Fine Organic Synthesis |
Authors: | Ishiyama, Tatsuo Browse this author →KAKEN DB |
Keywords: | diboron | α,β-unsaturated carbonyl compound | aromatic compound | 1, 4-addition | C-H borylation | copper catalyst | iridium catalyst | palladium catalyst | organoboron compound |
Issue Date: | 2003 |
Publisher: | 有機合成化学協会 |
Journal Title: | Journal of Synthetic Organic Chemistry, Japan |
Volume: | 61 |
Issue: | 12 |
Start Page: | 1176 |
End Page: | 1185 |
Publisher DOI: | 10.5059/yukigoseikyokaishi.61.1176 |
Abstract: | Recent studies on the developments of the metal-catalyzed new borylation reactions by bis- (pinacolato)diboron (1) are described. The 1, 4-addition of 1 to a,/3-unsaturated carbonyl compounds and nitriles proceeds in the presence of a catalytic amount of CuCl and KOAc in DMF. Subsequent treatment of the reaction mixture with water produces /3-boryl ketones, aldehydes, esters, and nitriles. Vinyl- and allylboron compounds are also obtained by the reactions of 1 with alkynes or allyl halides when using a stoichiometric amount of CuCl and KOAc. The aromatic C-H borylation of arenes or heteroarenes by 1 is effectively catalyzed by a combination of 1/2 [Ir(OMe) (COD)] 2 and 4, 4'-di-tert-butyl-2, 2'-bipyridine in hexane. The high activity of the catalyst allows the formation of aryl- and heteroarylboron compounds in high yields at room temperature from equimolar equivalents of 1 and substrate. The direct borylation of alkylarenes by 1 catalyzed by Pd/C exclusively occurs via benzylic C-H activation to give benzylboron compounds. |
Type: | article (author version) |
URI: | http://hdl.handle.net/2115/56516 |
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: 石山 竜生
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