448212-00-8Relevant articles and documents
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
Ishiyama, Tatsuo,Takagi, Jun,Kamon, Akihiro,Miyaura, Norio
, p. 284 - 290 (2003)
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 K
Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C3-Synthons
Wienhold, Max,Molloy, John J.,Daniliuc, Constantin G.,Gilmour, Ryan
supporting information, p. 685 - 689 (2020/11/30)
Modular β-borylacrylates have been validated as programmable, ambiphilic C3-synthons in the cascade annulation of 2-halo-phenol derivatives to generate structurally and electronically diverse coumarins. Key to this [3+3] disconnection is the BPin unit which serves a dual purpose as both a traceless linker for C(sp2)–C(sp2) coupling, and as a chromophore extension to enable inversion of the alkene geometry via selective energy transfer catalysis. Mild isomerisation is a pre-condition to access 3-substituted coumarins and provides a handle for divergence. The method is showcased in the synthesis of representative natural products that contain this venerable chemotype. Facile entry into π-expanded estrone derivatives modified at the A-ring is disclosed to demonstrate the potential of the method in bioassay development or in drug repurposing.
CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids
Link, Achim,Zhou, Yujing,Buchwald, Stephen L.
supporting information, p. 5666 - 5670 (2020/07/24)
The direct enantioselective copper hydride (CuH)-catalyzed synthesis of β-chiral amides from α,β-unsaturated carboxylic acids and secondary amines under mild reaction conditions is reported. The method utilizes readily accessible carboxylic acids and tolerates a variety of functional groups in the β-position including several heteroarenes. A subsequent iridium-catalyzed reduction to γ-chiral amines can be performed in the same flask without purification of the intermediate amides.
Triple copper catalysis for the synthesis of vinyl triazoles
Baldassari, Lucas L.,Cechinatto, Eduardo A.,Moro, Angélica V.
, p. 3556 - 3560 (2019/07/09)
Herein, we report our studies on the synthesis of vinyl 1,2,3-triazoles through a one-pot sequence, enabled by the same copper catalyst, of three different reactions: hydroboration involving an alkyne, azidation for a vinyl boronate and azide-alkyne cyclo
