Li Xin, Si Weili, Liu Zhanhui, Qian Haitao, Wang Tingxue, Leng Shengnan, Sun Jinwei, Jiao Yan, Zhang Xuan
School of Chemistry and Materials Science, Institute of Advanced Materials and Flexible Electronics (IAMFE), Nanjing University of Information Science and Technology, 219 Ningliu Road, Nanjing 210044, China.
Key Laboratory of Flexible Electronics (KLOFE) and Institute of Advanced Materials (IAM), Nanjing Tech University (NanjingTech), 30 South Puzhu Road, Nanjing 211800, China.
Org Lett. 2022 Jun 10;24(22):4070-4074. doi: 10.1021/acs.orglett.2c01525. Epub 2022 Jun 1.
Reactions involving an alkyl radical generated from a primary alcohol by photochemistry are rare and challenging. Herein, we present a photocatalyst- and metal-free approach that enables the generation of an alkyl radical from the corresponding alcohol and the subsequent C(sp)-C(sp) bond formation with activated olefin, via an alkyl thianthrenium salt/Hantzsch ester electron donor-acceptor complex. This protocol for the conversion of a C-OH bond to a C-C bond is highly functionality tolerant and can successfully be used in late-stage functionalization of pharmaceuticals.
涉及通过光化学从伯醇生成烷基自由基的反应很少见且具有挑战性。在此，我们提出了一种无光催化剂和无金属的方法，该方法能够通过烷基二苯并噻吩鎓盐/汉斯酯电子供体-受体络合物从相应的醇生成烷基自由基，并随后与活化烯烃形成C(sp)-C(sp)键。这种将C-OH键转化为C-C键的方法对官能团具有高度耐受性，并且可以成功用于药物的后期官能团化。
