Brønsted Acid Promoted Sulfonylation of Propargylic Alcohols: Synthesis of Triaryl Allenyl Sulfones under Mild Conditions

Abstract

An efficient and practical approach for the synthesis of triaryl allenyl sulfones from easily accessible propargylic alcohols was developed, by using sodium sulfinates as a sulfonyl source in the presence of Brønsted acid. The reaction proceeded via allenyl carbocation as the key intermediate and was followed by a nucleophilic attack of sodium sulfinates to produce allenyl sulfones in moderate to excellent yields.

Base-catalyzed addition of silylacetylenes to ketones: a route to protected tertiary propargyl alcohols

“…Propargyl alcohols are ubiquitous building blocks in chemical synthesis, being highly valued for their widespread application as valuable synthetic intermediates or medicinally relevant molecules themselves. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] They participate in a diverse array of transformations, owing this to their multifunctionality, and thereby being the subject of numerous studies. Protected propargyl alcohols can be accessed via well-developed stoichiometric methods, including mainly the use of a combination of propargyl alcohol, chlorosilane and organolithium reagent (Fig.…”