Synthesis of Various α-Substituted Alkenyl Sulfoxides from Alkynes and β-Sulfinyl Esters

Methods to synthesize alpha-substituted alkenyl sulfoxides are highly useful as they are widely used to construct diverse molecules of high synthetic importance. We have described a synthetic route for expedient access to the numerous alpha-substituted alkenyl sulfoxides from alkynes and beta-sulfinyl esters. This protocol exhibits a vast substrate scope, readily accommodates a wide range of functional groups, and is scalable in a gram-scale. Besides, we demonstrated a direct synthesis of alkenyl sulfoxides from thiols via the in situ generation of the requisite beta-sulfinyl ester. The ensuing alpha-substituted alkenyl sulfoxide product was readily transformed into benzofuran and sulfonyl derivatives. Mechanistic investigations were done to comprehend the reaction mechanism.

Automated summary

The methods for synthesizing alpha-substituted alkenyl sulfoxides are highly valuable for constructing diverse molecules. This study presents a synthetic route for accessing alpha-substituted alkenyl sulfoxides from alkynes and beta-sulfinyl esters, with a wide substrate scope and scalability. Additionally, a direct synthesis of alkenyl sulfoxides from thiols was demonstrated, with the resulting products easily transformed into benzofuran and sulfonyl derivatives. Mechanistic investigations were conducted to understand the reaction mechanism.