Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Direct Formation of Carbon(sp3)–Heteroatom Bonds from RhIII To Produce Methyl Iodide, Thioethers, and Alkylamines

Direct Formation of Carbon(sp3)–Heteroatom Bonds from RhIII To Produce Methyl Iodide, Thioethers, and Alkylamines
Karen I. Goldberg, Karena A. Smoll, Tyler E. Stevens
Thermolysis of the RhIII–Me complex (DPEphos)RhMeI2 (1) results in reductive elimination of MeI. Mechanistic studies are consistent with SN2 attack by I− at the RhIII–Me group via two separate competing paths. Addition of sulfur and nitrogen nucleophiles allows effective competition and formation of C(sp3)–S and C(sp3)–N coupled products in high yields. C(sp3)–N bond formation is second-order in amine, consistent with amine substitution of iodide at the metal followed by nucleophilic attack at carbon by a second amine.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b04169

DOI: 10.1021/jacs.7b04169

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