Mandal Tanumoy, Das Sanju, Maji Rohan, De Sarkar Suman
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur-741246, West Bengal, India.
Org Lett. 2023 Oct 27;25(42):7727-7732. doi: 10.1021/acs.orglett.3c03099. Epub 2023 Oct 16.
An electron donor-acceptor (EDA)-triggered hydrogen atom transfer (HAT) process is developed for the efficient generation of an α-alkoxy radical from cyclic ethers to synthesize exocyclic alkenylated ethers with exclusive -selectivity. A judiciously chosen donor-acceptor pair (DABCO and maleimide) serves as the desired HAT reagent under visible light irradiation without using any photocatalyst or peroxide. A wide variety of substrates were explored to demonstrate the diverse applicability and practical viability of this cross-dehydrogenative transformation. Detailed mechanistic studies revealed a radical reaction pathway under the oxidative environment.
开发了一种电子供体-受体（EDA）引发的氢原子转移（HAT）过程，用于从环醚高效生成α-烷氧基自由基，以专一的 - 选择性合成环外烯基化醚。在可见光照射下，精心选择的供体-受体对（1,4-二氮杂双环[2.2.2]辛烷和马来酰亚胺）用作所需的HAT试剂，无需使用任何光催化剂或过氧化物。探索了多种底物以证明这种交叉脱氢转化的多样适用性和实际可行性。详细的机理研究揭示了氧化环境下的自由基反应途径。
