Pd-Catalyzed C-S Activation/Isocyanide Insertion/Hydrogenation Enables a Selective Aerobic Oxidation/Cyclization
Pd-Catalyzed C-S Activation/Isocyanide Insertion/Hydrogenation Enables a Selective Aerobic Oxidation/Cyclization
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DOI：
10.1021/acs.orglett.6b01780
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发表时间：
2016-08-19
期刊：
影响因子：
5.2
通讯作者：
Wang, Mang
中科院分区：
文献类型：
--
作者：
Chang, Jian;Liu, Bangyu;Wang, Mang
硫代有机物与异腈的独特酰亚胺化赋予了前所未有的好氧氧化过程。在Pd（Ph 3 P）（2）C-12催化下，在Ph 3SiH存在下，在氮气保护下，α-芳基烯酮二硫代缩醛与异腈发生C-S键活化、异腈迁移插入、加氢、选择性有氧氧化和分子内亲核加成反应，生成5-羟基-α，β-不饱和γ-内酰胺。
Unique imidoylation of thioorganics with isocyanides endows an unprecedented aerobic oxidation process. Catalyzed by Pd(Ph3P)(2)C-12 in the presence of Ph3SiH under N-2 then upon exposure to air, a wide range of alpha-aryl ketene dithioacetals react with isocyanide to afford 5-hydroxy-alpha,beta-unsaturated gamma-lactams via a C-S bond activation, isocyanide migratdry insertion, hydrogehatioh, selective aerobic oxidation, and intramolecular nucleophilic addition sequence.