5589-62-8Relevant articles and documents
Combined Cyanoborylation, C-H Activation Strategy for Styrene Functionalization
Ansel, Annabel Q.,Montgomery, John
supporting information, p. 8538 - 8543 (2020/11/12)
A one-pot multicomponent copper-catalyzed protocol for borylation/ortho-cyanation of styrene derivatives followed by a Suzuki-Miyaura coupling provides a platform to explore the factors that control the selectivity between distal or proximal functionalization of arenes. The development of divergent nitrile-directed C-H functionalization (acetoxylation, pivalation, and methoxylation) offers an effective approach to rapidly increase synthetic complexity. Finally, the development of a mild reductive decyanation allows a traceless method to access functionalized biaryl motifs.
Chemoselectivity for Alkene Cleavage by Palladium-Catalyzed Intramolecular Diazo Group Transfer from Azide to Alkene
Frost, Grant B.,Mittelstaedt, Michaela N.,Douglas, Christopher J.
supporting information, p. 1727 - 1732 (2019/01/09)
Alkenes can be cleaved by means of the (3+2) cycloaddition and subsequent cycloreversion of 1,3-dipoles, classically ozone (O3), but the azide (R?N3) variant is rare. Chemoselectivity for these azide to alkene diazo group transfers (DGT) is typically disfavored, thus limiting their synthetic utility. Herein, this work discloses a palladium-catalyzed intramolecular azide to alkene DGT, which grants chemoselectivity over competing aziridination. The data support a catalytic cycloreversion mechanism distinct from other known metal-catalyzed azide/alkene reactions: nitrenoid/metalloradical and (3+2) cycloadditions. Kinetics experiments reveal an unusual mechanistic profile in which the catalyst is not operative during the rate-controlling step, rather, it is active during the product-determining step. Catalytic DGT was used to synthesize N-heterocyclic quinazolinones, a medicinally relevant structural core. We also report on the competing aziridination and subsequent ring expansion to another N-heterocyclic core structure of interest, benzodiazepinones.
Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides
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Page/Page column 77-78, (2020/01/09)
The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.
