Rhodium-catalyzed divergent dehydroxylation/alkenylation of hydroxyisoindolinones with vinylene carbonate

Literature Information

Publication Date 2023-11-02
DOI 10.1039/D3CC03760F
Impact Factor 6.222
Authors

Jiang Nan, Lu Liang


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Abstract

Herein, a novel organic transformation involving rhodium-catalyzed divergent dehydroxylation/alkenylation of hydroxyisoindolinone with vinylene carbonate is reported, and a series of architecturally rigid and widely used spirolactams are obtained with excellent functional group tolerance and high selectivity. Remarkably, the promising vinylene carbonate reagent presents a distinct chemical reactivity as a vinyl-oxygen cyclic synthon and first transfers the C–H bond to spiroheterocycle scaffolds. Moreover, another chemoselectivity, direct dehydrogenative coupling with vinylene carbonate, is also presented. This protocol is compatible with green chemistry and only releases H2O and CO2 as byproducts.

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Contents list

Front/Back Matter

DOI: 10.1039/C3CP90162A

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Chemical Communications

Chemical Communications
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