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Transition Metal-Free Radical α-Oxy C−H Cyclobutylation via Photoinduced Hydrogen Atom Transfer
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-05-12 , DOI: 10.1002/adsc.202200281
Han Gao 1 , Lin Guo 2 , Chengcheng Shi 1 , Yining Zhu 1 , Chao Yang 2 , Wujiong Xia 2
Affiliation  

A transition-metal-free photoinduced radical-mediated α-oxy C−H cyclobutylation reaction of bicyclo[1.1.0]butane (BCB) compounds was described. In this protocol, α-oxy C(sp3)−H motifs including ethers and alcohols were activated via photocatalytic conditions, releasing the ring strain of BCBs and generating 1,3-disubstituted cyclobutanes in 40–80% yields. Control experiments and Stern-Volmer quenching experiments indicated that the reaction proceeded through the generation of α-oxy carbon-centered radical intermediates by photoinduced hydrogen atom transfer (HAT) process.

中文翻译:

通过光致氢原子转移的过渡金属自由基 α-氧 C-H 环丁基化

描述了双环[1.1.0]丁烷(BCB)化合物的无过渡金属光诱导自由基介导的α-氧基C-H环丁基化反应。在该协议中,通过光催化条件激活包括醚和醇在内的α-氧基 C( sp 3 )-H 基序,释放 BCB 的环应变并以 40-80% 的产率生成 1,3-二取代环丁烷。对照实验和 Stern-Volmer 猝灭实验表明,该反应通过光致氢原子转移 (HAT) 过程生成以 α-氧碳为中心的自由基中间体进行。
更新日期:2022-05-12
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