1134-62-9Relevant articles and documents
Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with organolithium reagents
Bos, Pieter H.,Rudolph, Alena,Perez, Manuel,Fananas-Mastral, Martin,Harutyunyan, Syuzanna R.,Feringa, Ben L.
, p. 1748 - 1750 (2012)
A highly efficient method is reported for the asymmetric ring opening of oxabicyclic alkenes with organolithium reagents. Using a copper/chiral phosphoramidite complex together with a Lewis acid (BF3· OEt2), full selectivity for the anti isomer and excellent enantioselectivities were obtained for the ring opened products.
Palladium-Catalyzed Cross-Coupling of Superbase-Generated C(sp3) Nucleophiles
Freure, Garrett P. R.,Lavertu, Jean-Danick E.,Newman, Stephen G.,Skrotzki, Eric A.
, p. 12258 - 12263 (2021/10/26)
A range of methods has been investigated recently for the arylation of weakly acidic C(sp3)-H bonds, primarily exploiting directed metalation with a transition metal catalyst or radical formation via hydrogen atom transfer. In this work, a classical base-mediated approach is taken, exploiting the ability of organometallic superbases to metalate very weakly acidic (pKa> 40) C-H bonds. Conditions are developed with eithern-BuLi/diamine orn-BuLi/KOtBu superbases to enable metalation to occur with high selectivity. Organolithium nucleophiles can be directly used in cross-coupling, or organozincs can be formed to enable reactions with functional group-dense organohalides.
Unexpected formation of aryl ketones by palladium-catalyzed coupling of aryl bromides with vinylic acetates
Jean, Mickael,Renaulty, Jacques,Uriac, Philippe,Capet, Marc,Van De Weghe, Pierre
, p. 3623 - 3625 (2008/02/12)
A palladium-catalyzed coupling reaction of aryl bromides with vinylic acetates in the presence of tributyitin methoxide has been described. Unexpected formation of aryl ketones was obtained. Preliminary mechanistic studies indicated that the reaction proceeded by the addition of the aryl moiety in the coordination sphere of palladium to a ketene.