Verdazyl Radical Building Blocks: Synthesis, Structure, and Sonogashira Cross-Coupling Reactions

Verdazyl Radical Building Blocks: Synthesis, Structure, and Sonogashira Cross-Coupling Reactions Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2018, Volume: 2018, Number: 34, Pages: 4802-4811 Pages count : 10 DOI: 10.1002/ejoc.201701783

Tags

Verdazyl radicals; Nitrogen heterocycles; Cross-coupling; Density functional calculations

Authors

Petunin Pavel V. ^1,2 , Martynko Ekaterina A. ¹ , Trusova Marina E. ¹ , Kazantsev Maxim S. ^2,3 , Rybalova Tatyana V. ^2,3 , Valiev Rashid R. ^1,4 , Uvarov Mikhail N. ⁵ , Mostovich Evgeny.A. ^2,3 , Postnikov Pavel S. ¹

Affiliations

1	(Данные Web of science) Tomsk Polytech Univ, Tomsk 634050, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
4	(Данные Web of science) Tomsk State Univ, Tomsk 634050, Russia
5	(Данные Web of science) Russian Acad Sci, VV Voevodsky Inst Chem Kinet & Combust, Siberian Branch, Novosibirsk 630090, Russia

A general and effective method for the synthesis of 3-phenylveradzyl radicals bearing a variety of iodophenyl substituents has been developed. The synthesized radicals have been characterized by ESR, UV/Vis spectroscopy, and cyclic voltammetry. Structures of biphenyl-substituted radicals have been solved by X-ray crystal structure analysis. The synthesized iodoverdazyls are applicable in the Sonogashira coupling reaction for the preparation of a wide range of ethynyl derivatives. Both N-2 and C-6 substituents were functionalized through Sonogashira coupling.

Petunin P.V. , Martynko E.A. , Trusova M.E. , Kazantsev M.S. , Rybalova T.V. , Valiev R.R. , Uvarov M.N. , Mostovich E.A. , Postnikov P.S.
Verdazyl Radical Building Blocks: Synthesis, Structure, and Sonogashira Cross-Coupling Reactions
European Journal of Organic Chemistry. 2018. V.2018. N34. P.4802-4811. DOI: 10.1002/ejoc.201701783 WOS Scopus РИНЦ OpenAlex

Published online:	Mar 30, 2018
Published print:	Sep 16, 2018

Web of science:	WOS:000444540900019
Scopus:	2-s2.0-85053324309
Elibrary:	35723140
OpenAlex:	W2792975557

DB	Citing
Web of science	26
Scopus	23
Elibrary	29
OpenAlex	27