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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)
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: 石山 竜生

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