Abstract
Treatment of (IMes)Fe(NTMS2)2 with 4 equiv of methanesulfonyl chloride (MsCl = MeSO2Cl) resulted in a complex reaction sequence involving substitution of two TMS groups for Ms, followed by the unexpected C(sp3)–H bond activation of Ms and subsequent C(sp3)–C(sp3) bond formation to generate the bimetallic Fe complex, [IMesH]2[Cl2Fe(N(TMS)SO2(CH2)2SO2N(TMS))2FeCl2] (1) (IMes = 1,3-bis(2,4,6-trimethylphenyl)-imidazole-2-ylidene; TMS = SiMe3). Extending this C–H activation/C–C bond-forming chemistry to larger alkylsulfonyl chloride chains (i.e., Et and Bu) similarly resulted in C–C coupling, but with decreased chemoselectivity. Detailed mechanistic studies, including using possible intermediate model compounds, were performed in order to elucidate a unifying mechanism for this previously unknown avenue to C(sp3)–C(sp3) bond formation.
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