Nucleophilic C-H functionalization of arenes: a new logic of organic synthesis / Chupakhin Oleg N.,Charushin Valery N. // PURE AND APPLIED CHEMISTRY. - 2017. - V. 89, l. 8. - P. 1195-1208.

ISSN/EISSN:

0033-4545 / 1365-3075

Type:

Article; Proceedings Paper

Abstract:

Direct metal-free C-H functionalization of arenes with nucleophiles is a new chapter in the chemistry of aromatics. Comprehensive studies on nucleophilic substitution of hydrogen in arenes (the S-N(H) reactions), including mechanisms, intermediates, mathematic and electrochemical modeling, kinetics, electron-transfer, etc. have shown that this is not the hydride ion, but C-H proton is departed, and this process is facilitated by the presence of an appropriate oxidant or an auxiliary group. The S-N(H) reactions, as a part of the general C-H functionalization concept, change the logic of organic synthesis. They open new opportunities, avoiding incorporation of good leaving groups or other auxiliaries in an aromatic ring, as a prefunctionalization step, thus providing a better correspondence to the principles of green chemistry.

Author keywords:

arenes and hetarenes; C-H functionalization; dye-sensitizers for solar cells; eliminative and oxidative mechanisms; intermediate adducts; medicinal chemistry; Mendeleev XX; nucleophilic displacement o AROMATIC-SUBSTITUTION; GREEN CHEMISTRY; HYDROGEN; OXIDATION; PYRIMIDINES; NITROARENES; S-N(H); THIOCYANATION; NITROBENZENE; HETARENES

DOI:

10.1515/pac-2017-0108

Web of Science ID:

ISI:000410090000015

Соавторы в МНС:

Другие поля

Поле	Значение
Month	AUG
Note	20th Mendeleev Congress on General and Applied Chemistry (Mendeleev), Ekaterinburg, RUSSIA, SEP 21-26, 2016
Organization	IUPAC
Publisher	WALTER DE GRUYTER GMBH
Address	GENTHINER STRASSE 13, D-10785 BERLIN, GERMANY
Language	English
EISSN	1365-3075
Keywords-Plus	AROMATIC-SUBSTITUTION; GREEN CHEMISTRY; HYDROGEN; OXIDATION; PYRIMIDINES; NITROARENES; S-N(H); THIOCYANATION; NITROBENZENE; HETARENES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	chupakhin@ios.uran.ru
Funding-Acknowledgement	Russian Federation {[}3656-2014.310]
Funding-Text	This work was supported by the grant no. 3656-2014.310 for Leading Scientific Schools of the Russian Federation.
Number-of-Cited-References	57
Usage-Count-Last-180-days	6
Usage-Count-Since-2013	6
Journal-ISO	Pure Appl. Chem.
Doc-Delivery-Number	FG3QD