4-Sulfanylmethyl- and 4-sulfonylmethyl-substituted N,N′-diarylimidazolium salts as new proligands in the synthesis of Pd complexes with N-heterocyclic carbenes

4-Sulfanylmethyl- and 4-sulfonylmethyl-substituted N,N′-diarylimidazolium salts as new proligands in the synthesis of Pd complexes with N-heterocyclic carbenes Научная публикация

Журнал

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Вых. Данные

Год: 2024, Том: 73, Номер: 4, Страницы: 917-931 Страниц : 15 DOI: 10.1007/s11172-024-4205-y

Авторы

Shevchenko M.A. ¹ , Pasyukov D.V. ¹ , Minyaev M.E. ² , Chernyshev V.M. ¹

Организации

1	Platov South-Russian State Polytechnic University (NPI), 132 ul. Prosveschenya, 346428, Novocherkassk, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

The reaction of readily available N,N′-diaryl-4-chloromethylimidazolium chlorides with thiols afforded 4-(alkyl)arylsulfanylmethyl-N,N′-diarylimidazolium salts. The oxidation of these salts with hydrogen peroxide catalyzed by ammonium paramolybdate gave the previously unknown 4-(alkyl)arylsulfonylmethyl-N,N′-diarylimidazolium salts. The synthesized imidazolium salts can be used as sources of N-heterocyclic carbenes (NHCs). The conditions were found for the selective palladation of these compounds involving the C(2) atom of the imidazole ring. Palladium complexes with NHC ligands functionalized with RSCH2 and RSO2CH2 groups were synthesized. The potential applicability of these complexes as catalysts for cross-coupling reactions was demonstrated.

Shevchenko M.A. , Pasyukov D.V. , Minyaev M.E. , Chernyshev V.M.
4-Sulfanylmethyl- and 4-sulfonylmethyl-substituted N,N′-diarylimidazolium salts as new proligands in the synthesis of Pd complexes with N-heterocyclic carbenes
Russian Chemical Bulletin. 2024. V.73. N4. P.917-931. DOI: 10.1007/s11172-024-4205-y WOS Scopus OpenAlex

≡ Web of science:	WOS:001235375600034
≡ Scopus:	2-s2.0-85192196520
≡ OpenAlex:	W4396700192