Stereoselective Synthesis of Z -Styryl Sulfides from Nucleophilic Addition of Arylacetylenes and Benzyl Thiols.

Tarun Kumar Dinda, Syed Ramizul Kabir,Prasenjit Mal

The Journal of organic chemistry(2023)

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摘要
The stereoselective synthesis of -Markovnikov styryl sulfides via an anionic thiolate-alkyne addition reaction was achieved when the terminal alkynes and benzyl mercaptans were reacted using BuOLi (0.5 equiv) in EtOH under ambient conditions. Exclusive stereoselectivity (ca. 100%) was achieved by stereoelectronic control -periplanar and -Markovnikov addition of benzylthiolates to phenylacetylenes. Solvolysis of lithium thiolate ion pairs in ethanol significantly suppresses the competing formation of the isomer. A remarkable enhancement of the -selectivity under a longer reaction time was observed.
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关键词
benzyl thiols,arylacetylenes,synthesis,nucleophilic addition,sulfides
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