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Nickel(II)-Catalyzed Formal [3+2] Cycloadditions between Indoles and Donor–Acceptor Cyclopropanes
dc.contributor.author | Quezada, Víctor | |
dc.contributor.author | Castroagudín, Mariña | |
dc.contributor.author | Verdugo, Felipe | |
dc.contributor.author | Ortiz, Sergio | |
dc.contributor.author | Zaragoza, Guillermo | |
dc.contributor.author | Nachtigall, Fabiane M. | |
dc.contributor.author | Reis, Francisco A. A. | |
dc.contributor.author | Castro-Alvarez, Alejandro | |
dc.contributor.author | Santos, Leonardo S. | |
dc.contributor.author | Nelson, Ronald | |
dc.date.accessioned | 2024-05-21T07:23:55Z | |
dc.date.available | 2024-05-21T07:23:55Z | |
dc.date.issued | 2024 | |
dc.identifier | 10.3390/molecules29071604 | |
dc.identifier.issn | 14203049 | |
dc.identifier.uri | https://hdl.handle.net/20.500.12728/11280 | |
dc.description.abstract | This article describes the development of a nickel-catalyzed regio- and diastereoselective formal [3+2] cycloaddition between N-substituted indoles and donor–acceptor cyclopropanes to synthesize cyclopenta[b]indoles. Optimized reaction conditions provide the desired nitrogen-containing cycloadducts in up to 93% yield and dr 8.6:1 with complete regioselectivity. The substrate scope showed high tolerance to various substituted indoles and cyclopropanes, resulting in the synthesis of six new cyclopenta[b]indoles and the isolation of five derivatives previously reported in the literature. In addition, a mechanistic proposal for the reaction was studied through online reaction monitoring by ESI-MS, allowing for the identification of the reactive intermediates in the Ni(II) catalyzed process. X-ray crystallography confirmed the structure and relative endo stereochemistry of the products. This method enables the fast and efficient construction of fused indolines from readily accessible starting materials. © 2024 by the authors. | es_ES |
dc.description.sponsorship | Universidad Católica del Norte, UCN; Dirección General de Postgrado; Vicerrectoría de Investigación y Desarrollo Tecnológico; Agencia Nacional de Investigación y Desarrollo, ANID, (3190118, 3210175, 21221447); FONDECYT-ANID, (1220618, 1210576); VRIDT-UCN, (20230803020-VRIDT-UCN) | es_ES |
dc.language.iso | en | es_ES |
dc.publisher | Multidisciplinary Digital Publishing Institute (MDPI) | es_ES |
dc.subject | cyclopenta[b]indoles | es_ES |
dc.subject | donor–acceptor cyclopropanes | es_ES |
dc.subject | indoles | es_ES |
dc.subject | nickel catalyzed | es_ES |
dc.subject | [3+2] cycloaddition | es_ES |
dc.title | Nickel(II)-Catalyzed Formal [3+2] Cycloadditions between Indoles and Donor–Acceptor Cyclopropanes | es_ES |
dc.type | Article | es_ES |