Nickel(II)-Catalyzed Formal [3+2] Cycloadditions between Indoles and Donor–Acceptor Cyclopropanes

dc.creatorQuezada, Víctor
dc.creatorCastroagudín, Mariña
dc.creatorVerdugo, Felipe
dc.creatorOrtiz, Sergio
dc.creatorZaragoza, Guillermo
dc.creatorNachtigall, Fabiane M.
dc.creatorReis, Francisco A. A.
dc.creatorCastro-Alvarez, Alejandro
dc.creatorSantos, Leonardo S.
dc.creatorNelson, Ronald
dc.date2024-05-21T07:23:55Z
dc.date2024-05-21T07:23:55Z
dc.date2024
dc.date.accessioned2024-07-17T21:12:03Z
dc.date.available2024-07-17T21:12:03Z
dc.identifier10.3390/molecules29071604
dc.identifier14203049
dc.identifierhttps://hdl.handle.net/20.500.12728/11280
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/9509214
dc.descriptionThis 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.
dc.descriptionUniversidad 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)
dc.formatapplication/pdf
dc.formatapplication/octet-stream
dc.languageen
dc.publisherMultidisciplinary Digital Publishing Institute (MDPI)
dc.subjectcyclopenta[b]indoles
dc.subjectdonor–acceptor cyclopropanes
dc.subjectindoles
dc.subjectnickel catalyzed
dc.subject[3+2] cycloaddition
dc.titleNickel(II)-Catalyzed Formal [3+2] Cycloadditions between Indoles and Donor–Acceptor Cyclopropanes
dc.typeArticle


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