化学
烷基化
烷基
卤化物
芳基
有机化学
硫黄
炔丙基
位阻效应
药物化学
催化作用
作者
Andrew T. Champlin,Jonathan A. Ellman
标识
DOI:10.1021/acs.joc.3c00750
摘要
Sulfur alkylation of N-acyl sulfenamides with alkyl halides provides sulfilimines in 47% to 98% yields. A broad scope was established with a variety of aryl and alkyl sulfenamides, including for different N-acyl groups. Alkyl halides with different steric and electronic properties were effective inputs, including methyl, primary, secondary, benzyl, and propargyl halides. A proof-of-concept asymmetric phase-transfer alkylation was also demonstrated. A sulfilimine product was readily converted to an N-acyl and to a free sulfoximine, which represent important motifs in medicinal chemistry.
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