Tetrahedron Letters

A mild and highly convenient chemoselective alkylation of thiols using Cs 2 CO 3–TBAI

RN Salvatore, RA Smith, AK Nischwitz, T Gavin

文献索引：Salvatore, Ralph Nicholas; Smith, Robert A.; Nischwitz, Adam K.; Gavin, Terrence Tetrahedron Letters, 2005 , vol. 46, # 51 p. 8931 - 8935

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被引用次数: 66

摘要

A mild and improved method for the synthesis of thioethers has been developed. In the presence of cesium carbonate, tetrabutylammonium iodide, and DMF, various alkyl and aryl thiols underwent S-alkylation to afford structurally diverse sulfides in high yield. Unprotected mercaptoalcohols and thioamines reacted chemoselectively at the sulfur moiety exclusively. An example of a one-pot, solid-phase synthesis of a thioether is also described.