Banuprakash Goud S, Lal Dhakar Raju, Samanta Sampak
Department of Chemistry, Indian Institute of Technology Indore, Simrol, 453552, Madhya Pradesh, India.
Chem Asian J. 2024 Jan 15;19(2):e202300904. doi: 10.1002/asia.202300904. Epub 2023 Dec 7.
An in situ generated photoactive copper(I)-complex-catalyzed aziridination reaction of cyclic N-sulfonyl imines with α-aryl-substituted vinyl azides irradiated by blue-LEDs light is reported for the first time. This novel SET process represents a mild, sustainable, and pragmatic method for accessing synthetically resourceful sulfamidate-fused aziridines in acceptable chemical yields with excellent diastereoselectivities. Delightedly, pharmacologically attractive benzo[f][1,2,3]oxathiazepine dioxides and fused isoxazoline frameworks were achieved through our newly developed metal-free based ring-expansion techniques, highlighting the synthetic value of accessed aziridines. Finally, the possible mechanism for [2+1] aza-cyclization was presented based on the conduction of a series of control experiments.
首次报道了在蓝色发光二极管照射下，原位生成的光活性铜（I）配合物催化环状N-磺酰基亚胺与α-芳基取代的乙烯基叠氮化物的氮杂环丙烷化反应。这种新颖的单电子转移过程是一种温和、可持续且实用的方法，能够以可接受的化学产率和优异的非对映选择性获得具有合成价值的磺酰胺基稠合氮杂环丙烷。令人高兴的是，通过我们新开发的无金属扩环技术实现了具有药理学吸引力的苯并[f][1,2,3]氧杂噻嗪二氧化物和稠合异恶唑啉骨架，突出了所获得氮杂环丙烷的合成价值。最后，基于一系列对照实验的结果，提出了[2+1]氮杂环化的可能机理。
