期刊
CHEMISTRYSELECT
卷 6, 期 48, 页码 14054-14059出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.202103939
关键词
alkyne; alkenyl sulfoxide; synthetic methods; beta-sulfinyl ester; sulfenic acid
资金
- IISER Thiruvananthapuram
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.
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.
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