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. 2010 Dec 17;12(24):5688-91.
doi: 10.1021/ol102504b. Epub 2010 Nov 17.

Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes

Pei Chui Too  1 , Yi-Feng Wang, Shunsuke Chiba
Affiliations

Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes

Pei Chui Too et al. Org Lett. .

Abstract

A synthetic method of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes has been developed using [Cp*RhCl(2)](2)-NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C-H vinylation via ortho-rhodation and C-N bond formation of the putative vinyl rhodium intermediate on the oxime nitrogen, where the N-O bond of oxime derivatives could work as an internal oxidant to maintain the catalytic cycle.

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