A mild strategy for consecutive diazenylation and amination of indole moieties has been demonstrated. The functionalization occurs at C3 and C2 carbon atoms, respectively, at the indole scaffold in the presence of catalytic iodine and air at 40 °C in the 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) solvent. It is noteworthy that the aromatic amines are generated in situ by the reaction of aryl hydrazine with iodine. In general, bright red products are obtained in moderate to good yield. Control reactions are conducted to establish the reaction mechanism. Copyright © 2020 American Chemical Society.

Kshatresh Dutta Dubey

Chemistry

(SoNS) School of Natural Sciences

Subhabrata Sen

Sar S.

Tripathi A.

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Shiv Nadar University

Journal of Organic Chemistry

The first manganese-catalyzed cyclopropanation of indoles is reported in moderate to excellent yield with methyl-2-diazo-2-arylacetates. This new strategy involved acetyl (COCH 3 ) as the directing group and exhibited exceptional functional group tolerance. In the absence of stereodirecting groups the desired products were obtained as a mixture of diastereomers (7:3 → 8:2). Control experiments and DFT studies elucidated the probable pathway for the formation of cyclopropane-fused indole product. Deacetylation of the final products afforded both C3-substituted NH-indoles. © 2019 American Chemical Society.

Organic Letters

Directing-group-assisted manganese-catalyzed cyclopropanation of indoles

Chemical Communications

A rhodium(ii) catalysed domino synthesis of azepino fused diindoles from isatin tethered N-sulfonyl-1,2,3-triazoles and indoles

Privilege-Structure-Oriented Three-Component Asymmetric Aminomethylation: Assembly of Chiral 3-Aminomethyl Indolones

Nature Communications

Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction

Organic Process Research & Development

Palladium-Catalyzed C–N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C–N Bond Cleavage

Iodine-Catalyzed Aerobic Diazenylation-Amination of Indole Derivatives