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Divergent Reactivity of Rhodium(I) Carbenes Derived from Indole Annulations.

ABSTRACT: Rhodium(I) carbenes were generated from propargylic alcohol derivatives as the result of a dehydrative indole annulation. Depending on the choice of the electron-withdrawing group on the aniline nitrogen nucleophile, either a cyclopropanation product or dimerization product was obtained chemoselectively. Intramolecular hydroamidation occurred for the same type of propargylic alcohol derivatives when other transition-metal catalysts were employed.

SUBMITTER: Li X

PROVIDER: S-EPMC4612373 | biostudies-literature | 2015 Oct

REPOSITORIES: biostudies-literature

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Divergent Reactivity of Rhodium(I) Carbenes Derived from Indole Annulations.

Li Xiaoxun X Li Hui H Song Wangze W Tseng Po-Sen PS Liu Lingyan L Guzei Ilia A IA Tang Weiping W

Angewandte Chemie (International ed. in English) 20150907 44

Rhodium(I) carbenes were generated from propargylic alcohol derivatives as the result of a dehydrative indole annulation. Depending on the choice of the electron-withdrawing group on the aniline nitrogen nucleophile, either a cyclopropanation product or dimerization product was obtained chemoselectively. Intramolecular hydroamidation occurred for the same type of propargylic alcohol derivatives when other transition-metal catalysts were employed. ...[more]

PMID: 26480329

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