Microwave-assisted palladium-catalyzed C-C coupling versus nucleophilic aromatic substitution of hydrogen (S-N(H)) in 5-bromopyrimidine by action of bithiophene and its analogues / Verbitskiy Egor V.,Cheprakova Ekaterina M.,Zhilina Ekaterina F.,Kodess Mikhail I.,Ezhikova Marina A.,Pervova Marina G.,Slepukhin Pavel A.,Subbotina Julia O.,Schepochkin Aleksandr V.,Rusinov Gennady L.,Chupakhin Oleg N.,Charushin Valery N. // TETRAHEDRON. - 2013. - V. 69, l. 25. - P. 5164-5172.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

5-Bromopyrimidine reacts with 2,2'-bithiophene, {[}2,2':5',2 `']terthiophene and 2-phenylthiophene in the presence of a palladium catalyst to give 5-(het)aryl substituted pyrimidines due to the palladium-catalyzed aryl-aryl C-C coupling. However 5-bromo-4-(het)aryl-pyrimidines have been prepared from the same starting materials through the S-N(H)-reaction catalyzed by a Lewis acid. Conditions for both types of reactions were optimized. All components of the reaction mixtures, including by-products, have been elucidated by gas-liquid chromatography/mass-spectrometry. Evidence for the structure of 4- and 5-bithiophenyl-substituted pyrimidines has first been obtained by means of X-ray crystallography analysis. Molecular orbital calculations (TDDFT), as well as the redox and optical measurements for all new compounds have also been performed. (C) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

C-H bond activations; Nucleophilic aromatic substitution of hydrogen; Pyrimidines; Palladium; Microwave-assisted synthesis DIRECT ARYLATION; ARYL BROMIDES; HETEROAROMATICS; FUNCTIONALIZATION; SYSTEMS

DOI:

10.1016/j.tet.2013.04.062

Web of Science ID:

ISI:000319647600015

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUN 24
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	DIRECT ARYLATION; ARYL BROMIDES; HETEROAROMATICS; FUNCTIONALIZATION; SYSTEMS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	Verbitsky@ios.uran.ru
ResearcherID-Numbers	Subbotina, Julia/L-7131-2016
ORCID-Numbers	Subbotina, Julia/0000-0002-2227-0787
Funding-Acknowledgement	Ural Branch of the Russian Academy of Sciences {[}12-P-3-1014, 12-P-3-1030, 12-T-3-1025, 12-T-3-1031]; State Program for Supporting of Leading Scientific Schools of the Russian Federation {[}NSh 5505.20123]; Russian Foundation for Basic Research {[}12-03-31574-mol\_a, 13-03-96049-r\_ural\_a, 13-03-90606-Arm\_a]; Ministry of Education and Science of Russian Federation {[}8430, 8634]
Funding-Text	This work was supported by the Ural Branch of the Russian Academy of Sciences (Grants. No 12-P-3-1014, 12-P-3-1030, 12-T-3-1025, and 12-T-3-1031), the State Program for Supporting of Leading Scientific Schools of the Russian Federation (grant NSh 5505.20123) and the Russian Foundation for Basic Research (research projects No. 12-03-31574-mol\_a, 13-03-96049-r\_ural\_a, and 13-03-90606-Arm\_a), the Ministry of Education and Science of Russian Federation (projects No 8430 and 8634). J.O.S. thanks Compute Canada-Calcul Canada and West Grid for computing recourses. J.O.S. also thanks Prof. Arvi Rauk (University of Calgary, Canada) for his personal assistance and helpful advice.
Number-of-Cited-References	36
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	20
Journal-ISO	Tetrahedron
Doc-Delivery-Number	154BX