Sulfonylation of Propargyl Alcohols with Sulfinamides for the Synthesis of Allenyl Sulfones.

A regio- and chemoselective sulfonylation of propargyl alcohols with sulfinamides in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) was developed. It provided straightforward and mild access to multi-substituted allenyl sulfones by using sulfinamides as the sulfonyl sources. This transformation was promoted by HFIP and did not require any catalysts or oxidants, which allowed for the successful conversion of various tertiary and secondary propargyl alcohols into allenyl sulfones in high yields.

1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP)-Assisted Catalyst-Free Sulfonation of Allylic Alcohols with Sulfinyl Amides.

A highly regioselective and catalyst-free sulfonation of allylic alcohols with sulfinyl amides has been realized. Such a mix-and-go procedure provides a convenient approach to synthetically various allylic sulfones under mild reaction conditions. Furthermore, this novel reaction shows ample substrate scope and outstanding functional group tolerance and could also be scaled-up. Meanwhile, it is the first example that sulfinyl amides act as a powerful sulfur nucleophile in the reactions. 1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) as a solvent plays a critical role in allylic sulfonation.