Simple iodoalkyne-based organocatalysts for the activation of carbonyl compounds

Alegre-Requena, Juan V. ; Valero-Tena, Alberto ; Giménez Sonsona, Isaac ; Uriel, Santiago (Universidad de Zaragoza) ; Pérez Herrera, Raquel (Universidad de Zaragoza)

Resumen: A novel approach for the formation of bisindolylmethane derivatives (BIMs) is described as a proof of concept to evaluate the catalytic capacity of iodoalkynes. The use of these derivatives is reported as an example of simple halogen bond-based organocatalyst. This kind of activation has not been used before for the synthesis of bisindolylmethane derivatives 3. Interestingly, the preparation of 3-(1H-indol-3-yl)-1-phenylbutan-1-one (8) has been also achieved for the first time with an iodoalkyne derivative. We prove the efficiency of this family of new catalysts by developing a simple and easy operational methodology, opening the door to the development of alternative catalysts in the area of halogen bond-based organocatalysts.

Idioma: Inglés

DOI: 10.1039/c9ob02688f

Año: 2020

Publicado en: Organic & Biomolecular Chemistry 18, 8 (2020), 1594-1601
ISSN: 1477-0520

Factor impacto JCR: 3.876 (2020)

Categ. JCR: CHEMISTRY, ORGANIC rank: 13 / 57 = 0.228 (2020) - Q1 - T1

Factor impacto SCIMAGO: 0.923 - Biochemistry (Q1) - Physical and Theoretical Chemistry (Q1) - Organic Chemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA-FSE/E07-17R
Financiación: info:eu-repo/grantAgreement/ES/DGA-FSE/E47-17R
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2017-88091-P
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/PGC2018-093761-B-C31

Tipo y forma: Artículo (Versión definitiva)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)