open access

https://hdl.handle.net/2115/56516

Developments of New Catalytic Borylation Reactions Directed towards Fine Organic Synthesis

英語

organoboron compound

2003

有機合成化学協会

Journal of Synthetic Organic Chemistry, Japan

61(12)

1176-1185

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.

学術雑誌論文

Submitted Manuscript Under Review

0037-9980

1883-6526