A Rh()/phosphoric acid co-catalyzed three-component reaction of diazo-ketones with alcohols and azonaphthalenes: access to indole derivatives a formal [3 + 2]-cycloaddition

A novel dearomatization/rearomatization/cyclization oxonium ylide trapping process is well developed via a dirhodium( ii ) acetate and phosphoric acid cooperatively catalyzed multi-component reaction of diazo-ketones with alcohols and azonaphthalenes. This protocol provides an efficient route to syn...

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Published in:Organic & biomolecular chemistry 2020-12, Vol.18 (48), p.985-989
Main Authors: Yin, Xinru, Xu, Aimin, Hu, Jidi, Bao, Ming, Hu, Wenhao, Qian, Yu
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Summary:A novel dearomatization/rearomatization/cyclization oxonium ylide trapping process is well developed via a dirhodium( ii ) acetate and phosphoric acid cooperatively catalyzed multi-component reaction of diazo-ketones with alcohols and azonaphthalenes. This protocol provides an efficient route to synthesize N -substituted 1-amino-indole derivatives in good yield under mild reaction conditions. Rh( ii )/Phosphoric Acid co-catalyzed muti-component annulation was well established as a new efficient route to construct 1-amino-indole derivatives via dearomatization/rearomatization/cyclization process with in situ formed oxonium ylide.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob02189j