Article Early Access 2023 · 7 citations

Solvent-Mediated Tunable Regiodivergent C6-and N1-Alkylations of 2,3-Disubstituted Indoles with p-Quinone Methides

Adris, Douaa, Taskesenligil, Yunus, Akyildiz, Volkan, Essiz, Selcuk, Saracoglu, Nurullah

Abstract

Indium-catalyzed, solvent-enabled regioselective C6- or N1-alkylations of 2,3-disubstituted indoles with para-quinone methides are developed under mild conditions. Notably, highly selective and switchable alkylations were selectively achieved by adjusting the reaction conditions. Moreover, scalability and further transformations of the alkylation products are demonstrated, and this operationally simple methodology is amenable to the late-stage C6-functionalization of the indomethacin drug. The reaction pathways were explained with the support of experimental and density functional theory studies.

Keywords

C-H ALKYLATION 1,6-CONJUGATE ADDITION ENANTIOSELECTIVE SYNTHESIS ARYLATION FUNCTIONALIZATION 1,6-ADDITION DERIVATIVES 3-INDOLYLMETHANOLS ANTIDEPRESSANT ALLYLATION

WoS Categories

Chemistry, Organic

Sustainable Development Goals

Good Health and Well-being

Citation

Journal: JOURNAL OF ORGANIC CHEMISTRY
Year: 2023
ISSN: 0022-3263
eISSN: 1520-6904
DOI: 10.1021/acs.joc.2c02937
WoS UID: WOS:000936593000001

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