Solvent-Dependent Photochemistry for Diverse and Selective C-H Functionalization of 2-tert-Butyl-1,4-Benzoquinones
- Authors
- Ka, Cheol Hyeon; Lee, Da Seul; Cho, Eun Jin
- Issue Date
- Oct-2022
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- benzoquinone; C-H activation; hydrogen atom transfer; radicals; solvent effects
- Citation
- CHEMPHOTOCHEM, v.6, no.10
- Journal Title
- CHEMPHOTOCHEM
- Volume
- 6
- Number
- 10
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/58407
- DOI
- 10.1002/cptc.202200136
- ISSN
- 2367-0932
- Abstract
- Controlling a reaction to selectively produce a set of distinct valuable compounds from the same substrate is a highly attractive topic in synthetic chemistry. In this work, the solvent-dependent photochemistry of 2-tert-butyl-1,4-benzoquinones to achieve diverse C-H functionalization was investigated, which afforded three selective transformations: (1) intermolecular C-O bond formation in non-fluorinated alcoholic solvents; (2) perfluorinated hexafluoroisopropanol solvent-promoted intramolecular cyclization to afford coumaran derivatives; (3) 1,4-dioxane solvent-induced hydrogen atom transfer to afford 2-methylallyl hydroquinones.
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