Atom- and step-economical nucleophilic arylation of azaaromatics via electrochemical oxidative cross C-C coupling reactions / Chupakhin O. N.,Shchepochkin A. V.,Charushin V. N. // GREEN CHEMISTRY. - 2017. - V. 19, l. 13. - P. 2931-2935.

ISSN/EISSN:

1463-9262 / 1463-9270

Type:

Article

Abstract:

The synthesis of asymmetrical bi(het)aryls through direct functionalization of the C(sp(2))-H bond in azaaromatics with fragments of (hetero)aromatic nucleophiles has first been carried out under electrochemical oxidative conditions. This versatile method for C-C bond formation between two aryl fragments can be realized under very mild potential-controlled oxidative conditions, and it does require neither incorporation of any halogen atoms or other leaving groups, nor the use of metal catalysts. The use of the electrochemical S-N(H) methodology for modification of azaaromatic compounds has first been demonstrated.

Author keywords:

AROMATIC-SUBSTITUTION REACTIONS; PROTONATED 1,3-DIAZINES; HYDROGEN; CHEMISTRY; FUNCTIONALIZATION; DERIVATIVES; PHENOLS; ARENES

DOI:

10.1039/c7gc00789b

Web of Science ID:

ISI:000404609200003

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL 7
Publisher	ROYAL SOC CHEMISTRY
Address	THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Language	English
EISSN	1463-9270
Keywords-Plus	AROMATIC-SUBSTITUTION REACTIONS; PROTONATED 1,3-DIAZINES; HYDROGEN; CHEMISTRY; FUNCTIONALIZATION; DERIVATIVES; PHENOLS; ARENES
Research-Areas	Chemistry; Science \& Technology - Other Topics
Web-of-Science-Categories	Chemistry, Multidisciplinary; GREEN \& SUSTAINABLE SCIENCE \& TECHNOLOGY
Author-Email	chupakhin@ios.uran.ru
ORCID-Numbers	Shepochkin, Alexandr/0000-0001-7998-8311
Funding-Acknowledgement	Russian Science Foundation {[}14-13-01177]; Council on Grants of the President of the Russian Federation (Program for State Support of Leading Scientific Schools) {[}NSh-8922.2016.3]
Funding-Text	The research was financially supported by the Russian Science Foundation (Project No. 14-13-01177) and the Council on Grants of the President of the Russian Federation (Program for State Support of Leading Scientific Schools (Grant NSh-8922.2016.3)). The authors are thankful to Drs O. S. Eltsov and M. I. Kodess, coworkers of Ural Federal University and Institute of Organic Synthesis of the Russian Academy of Sciences for their assistance in the NMR experiments.
Number-of-Cited-References	30
Usage-Count-Last-180-days	11
Usage-Count-Since-2013	11
Journal-ISO	Green Chem.
Doc-Delivery-Number	EZ3KG