Hou Hao, Ou Wei, Su Chenliang
International Collaborative Laboratory of 2D Materials for Optoelectronics Science and Technology of Ministry of Education, Institute of Microscale Optoelectronics, Shenzhen University, Shenzhen 518060, P. R. China.
J Org Chem. 2024 Mar 15;89(6):4120-4127. doi: 10.1021/acs.joc.3c02953. Epub 2024 Mar 5.
Heteroatom-adjacent C(sp) radical cyclization of -arylacrylamides provides a straightforward pathway to synthesize valuable 3-functionalized oxindoles. Traditional cyclization reactions normally require harsh conditions or transition-metal catalysts. Here, we developed a metal-free, diversity-oriented synthesis of 3-functionalized oxindoles via photochemically induced selective cleavage of C(sp)-H bonds. A variety of 3-substituted oxindoles with functionalities such as ethers, polyhalogens, benzyl, and formyl groups can be obtained by a rational design. This strategy is characterized by its simple operation and mild conditions, aligning well with the developmental requirements for sustainable chemistry. The gram-scale continuous-flow synthesis and efficient construction of bioactive molecules highlight its practical utility.
芳基丙烯酰胺的杂原子邻位C(sp)自由基环化反应为合成有价值的3-官能化氧化吲哚提供了一条直接的途径。传统的环化反应通常需要苛刻的条件或过渡金属催化剂。在此，我们通过光化学诱导的C(sp)-H键选择性裂解，开发了一种无金属、面向多样性的3-官能化氧化吲哚合成方法。通过合理设计，可以得到各种具有醚、多卤素、苄基和甲酰基等官能团的3-取代氧化吲哚。该策略具有操作简单、条件温和的特点，与可持续化学的发展要求高度契合。克级连续流合成以及生物活性分子的高效构建突出了其实际应用价值。
