One‐Step Access to Heteroatom‐Functionalized Imidazol(in)ium Salts

One‐Step Access to Heteroatom‐Functionalized Imidazol(in)ium Salts Full article

Journal

Angewandte Chemie International Edition
ISSN: 1433-7851 , E-ISSN: 1521-3773

Output data

Year: 2022, Volume: 61, Number: 9, Article number : e202116131, Pages count : DOI: 10.1002/anie.202116131

Authors

Pasyukov Dmitry V. ¹ , Shevchenko Maxim A. ¹ , Shepelenko Konstantin E. ¹ , Khazipov Oleg V. ¹ , Burykina Julia V. ² , Gordeev Evgeniy G. ² , Minyaev Mikhail E. ² , Chernyshev Victor M. ¹ , Ananikov Valentine P. ²

Affiliations

1	Platov South-Russian State Polytechnic University (NPI), Prosveschenya 132, Novocherkassk, 346428, Russia
2	Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky Prospect 47, Moscow, 119991, Russia

Imidazolium salts have ubiquitous applications in energy research, catalysis, materials and medicinal sciences. Here, we report a new strategy for the synthesis of diverse heteroatom-functionalized imidazolium and imidazolinium salts from easily available 1,4-diaza-1,3-butadienes in one step. The strategy relies on a discovered family of unprecedented nucleophilic addition/cyclization reactions with trialkyl orthoformates and heteroatomic nucleophiles. To probe general areas of application, synthesized N-heterocyclic carbene (NHC) precursors were feasible for direct metallation to give functionalized M/carbene complexes (M=Pd, Ni, Cu, Ag, Au), which were isolated in individual form. The utility of the chloromethyl function for the postmodification of the synthesized salts and Pd/carbene complexes was demonstrated. The obtained complexes and imidazolium salts demonstrated good activities in Pd- or Ni-catalyzed model cross-coupling and C−H activation reactions

Pasyukov D.V. , Shevchenko M.A. , Shepelenko K.E. , Khazipov O.V. , Burykina J.V. , Gordeev E.G. , Minyaev M.E. , Chernyshev V.M. , Ananikov V.P.
One‐Step Access to Heteroatom‐Functionalized Imidazol(in)ium Salts
Angewandte Chemie International Edition. 2022. V.61. N9. e202116131 . DOI: 10.1002/anie.202116131 WOS Scopus OpenAlex

Web of science:	WOS:000746212100001
Scopus:	2-s2.0-85123464616
OpenAlex:	W4200427326

DB	Citing
OpenAlex	17
Scopus	14
Web of science	15