烯炔二烯酮的硫芳基化自由基环化反应
Thioarylative Radical Cyclization of Yne-Dienone.
作者信息
Mallick Rajendra K, Dutta Shubham, Vanjari Rajeshwer, Voituriez Arnaud, Sahoo Akhila K
机构信息
School of Chemistry , University of Hyderabad , Hyderabad 500046 , India.
Institut de Chimie des Substances Naturelles (ICSN), CNRS , 91198 Cedex Gif-sur-Yvette , France.
出版信息
J Org Chem. 2019 Aug 16;84(16):10509-10517. doi: 10.1021/acs.joc.9b01445. Epub 2019 Aug 1.
We herein demonstrated a -hydroxyphthalimide (NHPI)-mediated chemo- and regioselective radical cyclization of yne-dienone with thiols to construct 3-thioaryl bearing [6,6]-fused dihydrochromenone derivatives. This transformation tolerates common functional groups and has broad scope. The reaction proceeds via the attack of a thioaryl radical to alkyne over the activated Michael acceptor. The TEMPO quenching experiment suggests the involvement of a radical intermediate. Synthetic versatility of 3-thioaryldihydrochromenones is also showcased.
我们在此展示了α-羟基邻苯二甲酰亚胺（NHPI）介导的炔二烯酮与硫醇的化学和区域选择性自由基环化反应，以构建含3-硫芳基的[6,6]-稠合二氢色原酮衍生物。这种转化能耐受常见的官能团，适用范围广泛。该反应通过硫芳基自由基对活化的迈克尔受体上的炔烃的进攻而进行。TEMPO猝灭实验表明有自由基中间体参与。还展示了3-硫芳基二氢色原酮的合成多功能性。
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