Journal
CHEMPHOTOCHEM
Volume 6, Issue 10, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cptc.202200136
Keywords
benzoquinone; C-H activation; hydrogen atom transfer; radicals; solvent effects
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Funding
- Chung-Ang University Graduate Research Scholarship in 2021
- National Research Foundation of Korea [NRF-2020R1A2C2009636, NRF-2021R1A5A6002803]
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This work investigates the solvent-dependent photochemistry of 2-tert-butyl-1,4-benzoquinones and achieves three selective transformations under different solvent conditions.
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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