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Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with vinyl triflates β-substituted by a carbonyl group: efficient synthesis of β-boryl-α,β-unsaturated carbonyl compounds and their synthetic utility

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Title: Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with vinyl triflates β-substituted by a carbonyl group: efficient synthesis of β-boryl-α,β-unsaturated carbonyl compounds and their synthetic utility
Authors: Ishiyama, Tatsuo Browse this author →KAKEN DB
Takagi, Jun Browse this author
Kamon, Akihiro Browse this author
Miyaura, Norio Browse this author →KAKEN DB
Keywords: Bis(pinacolato)diboron
Vinyl triflate
Palladium catalyst
Vinylboronate
Cross-coupling
Issue Date: 7-Dec-2003
Publisher: Elsevier
Journal Title: Journal of Organometallic Chemistry
Volume: 687
Issue: 2
Start Page: 284
End Page: 290
Publisher DOI: 10.1016/S0022-328X(03)00611-9
Abstract: Cross-coupling reaction of bis(pinacolato)diboron with β-(trifluoromethanesulfonyloxy)-α,β-unsaturated carbonyl compounds was carried out in the presence of PdCl2(PPh3)2-2PPh3 (3 mol%) and KOPh in toluene or K2CO3 in dioxane for the synthesis of cyclic and acyclic β-boryl-α,β-unsaturated esters, amides, and ketones in high yields. The vinylboronates thus obtained readily participated in carbon-carbon bond formation, such as cross-coupling with vinyl triflates and 1,4-addition to α,β-unsaturated ketones.
Type: article (author version)
URI: http://hdl.handle.net/2115/56318
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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