Effect of In–CNHC Bonds on the Synthesis, Structure, and Reactivity of Dialkylindium Alkoxides: How Indium Compares to Gallium

作者: Martyna Cybularczyk , Maciej Dranka , Janusz Zachara , Paweł Horeglad

DOI: 10.1021/ACS.ORGANOMET.6B00510

关键词: Medicinal chemistryAdductAlkoxideOrganic chemistryIMesAlkylAlkoxy groupSIMesChemistryGalliumReactivity (chemistry)

摘要: The investigation of the reactivity dialkylindium alkoxides toward N-heterocyclic carbenes (NHCs) has shown that both character In–CNHC bond and alkyl alkoxide substituents have a significant effect on formation R2InOR(NHC) complexes distribution products. reactions simple dimethylindium with 1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene (SIMes) 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes) lead to monomeric Me2InOR(NHC), as by isolation Me2InOMe(NHC) (NHC = IMes (3), SIMes (4)). Compounds Me2InOR(NHC) are unstable in solution instantly disproportionate, which can be associated weaker comparison stable gallium analogues. As result, Me3In(NHC) (1), (2)) adducts, well Mitsubishi-type methylindium alkoxides, formed. exchange alkoxy group chelating (S)-methyl lactate (S-melac) resulted more s...

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