Efficient synthesis of isoquinolines in water by a Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids

Autor:	Huayue Wu, Qi Linjun, Jiuxi Chen, Tianxing Cheng, Xiaodong Wang, Zhaojun Li, Shuling Yu, Kun Hu, Yuanzhi Xia
Rok vydání:	2017
Předmět:	Acetonitriles 010405 organic chemistry Chemistry Intramolecular cyclization 010402 general chemistry 01 natural sciences Pollution 0104 chemical sciences Catalysis chemistry.chemical_compound Cascade reaction Functional group Environmental Chemistry Organic chemistry Density functional theory
Zdroj:	Green Chemistry. 19:1740-1750
ISSN:	1463-9270 1463-9262
DOI:	10.1039/c7gc00267j
Popis:	A palladium-catalyzed tandem reaction of 2-(cyanomethyl)benzonitriles or 2-(2-carbonylphenyl)acetonitriles with arylboronic acids in water has been developed for the first time. This reaction features good functional group tolerance and provides a new strategy for the synthesis of diverse isoquinolines under mild conditions. The use of water as the reaction medium makes the synthesis process environmentally benign. Preliminary mechanistic experiments indicate that the major reaction pathway involves carbopalladation of the C(sp3)–cyano group and subsequent intramolecular cyclization findings that were further supported by density functional theory (DFT) calculations.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::68a26e30615e60a6ec5c2a8d562719e3 https://doi.org/10.1039/c7gc00267j Zobrazit plný text záznamu