Highly Regioselective RhIII-Catalyzed Thiolation of N-Tosyl Acrylamides: General Access to (Z)-β-Alkenyl Sulfides
Highly Regioselective RhIII-Catalyzed Thiolation of N-Tosyl Acrylamides: General Access to (Z)-β-Alkenyl Sulfides
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高区域选择性 Rh-III 催化的 N-甲苯磺酰丙烯酰胺硫醇化：获得 (Z)-β-链烯基硫醚的一般途径
DOI：
10.1021/acs.orglett.8b02552
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发表时间：
2018-10-05
期刊：
影响因子：
5.2
通讯作者：
Ji, Shun-Jun
中科院分区：
文献类型：
--
作者：
Liu, Can;Fang, Yi;Ji, Shun-Jun
研究了铑催化N-对甲苯磺酰基丙烯酰胺与二硫键的区域选择性硫醇化反应。通过N-对甲苯磺酰胺辅助活化烯基C（sp（2））-H键，以中等至优异的产率合成了一系列（Z）-烯基硫醚，并具有良好的官能团耐受性。利用0.01摩尔% Rh-III催化剂获得高达7100的转换数（TON）。此外，二苯基二硒醚也被成功地应用于该反应，在相同的条件下，用于（Z）-β-烯基硒醚的构建。
A regioselective rhodium-catalyzed thiolation of N-tosyl acrylamides with readily available disulfides has been developed. Through N-tosylamide-assisted activation of the alkenyl C(sp(2))-H bond, a series of (Z)-alkenyl sulfides were constructed in moderate to excellent yields with good tolerance of functional groups. Turnover numbers (TONs) of up to 7100 were obtained utilizing 0.01 mol % Rh-III catalyst. In addition, diphenyl diselenide was also successfully applied to this reaction for the construction of (Z)-beta-alkenyl selenides under identical conditions.