Transition Metal‐Free Radical α‐Oxy C−H Cyclobutylation via Photoinduced Hydrogen Atom Transfer. Issue 13 (24th May 2022)

• Record Type: Journal Article
• Authors: Gao, Han; Guo, Lin; Shi, Chengcheng; Zhu, Yining; Yang, Chao; Xia, Wujiong
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 13(2022)
• Page Start: 2140
• Page End: 2145
• Publication Date: 2022-05-24
• Subjects: photoredox catalysis -- hydrogen atom transfer -- C−H activation -- strain release -- bicyclo[1.1.0]butane; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200281
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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( sp 3 )−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. Abstract :