Six- and seven-membered ring carbenes: Rational synthesis of amidinium salts, generation of carbenes, synthesis of Ag(I) and Cu(I) complexes |
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Authors: | Eugene L Kolychev Viacheslav V Shuntikov Mikhail S Nechaev |
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Institution: | a Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russian Federation b A.V. Topchiev Institute of Petrochemical Synthesis, RAS, Leninsky Prosp., 29, Moscow 119991, Russian Federation c A.N. Nesmeyanov Institute of Organoelement Compounds of RAS, Vavilov Str., 28, Moscow 119991, Russian Federation |
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Abstract: | Reactions of neat 1,3- and 1,4-dibromides with N,N′-diarylformamidines in the presence of diisopropylethylamine (DIPEA) afford corresponding amidinium salts in high yields (>80%). Six- and seven-membered ring amidinium salts bearing bulky Mes (2,4,6-Me3C6H2) and Dipp (2,6-iPr2C6H3) aryl groups were prepared using this method. Free six-membered ring carbene 6-Dipp was generated from amidinium salt using LiHMDS as a base. NHC-Ag(I) complexes were obtained by the reactions of amidinium salts with Ag2O. NHC complexes of Pd and Rh are not accessible by deprotonation of amidinium salts, nor by transmetallation of Ag(I) complexes. However NHC-Cu(I) complexes were obtained by transmetallation of NHC-Ag(I). Thus, transmetallation of six- and seven-membered NHC-Ag(I) complexes was documented for the first time. |
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Keywords: | N-heterocyclic carbene Amidinium salt Deprotonation Silver complex Copper complex Transmetallation |
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