Journal
ORGANIC LETTERS
Volume 23, Issue 20, Pages 8082-8087Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03090
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Funding
- National Natural Science Foundation of China [22088102, 21933007, 21861132004]
- Ministry of Science and Technology of China [2017YFA0206903]
- Strategic Priority Research Program of the Chinese Academy of Science [XDB17000000]
- Key Research Program of Frontier Sciences of the Chinese Academy of Science [QYZDY-SSW-JSC029]
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This study presents an aerobic metal-free, visible-light-induced regioselective thiolation of phenols with thiophenols, showing high functional group tolerance and selectivity. Mechanistic studies reveal the crucial role of disulfide radical cation in the visible-light catalysis of aerobic thiolation, allowing selective formation of sulfide or sulfoxide products with high activity in a one-pot reaction by controlling the equivalent ratio of substrates.
An aerobic metal-free, visible-light-induced regioselective thiolation of phenols with thiophenols is reported. The cross-coupling protocol exhibits great functional group tolerance and high regioselectivity. Mechanistic studies reveal that the disulfide radical cation plays a crucial role in the visible-light catalysis of aerobic thiolation. Simply controlling the equivalent ratio of substrates enables the selective formation of sulfide or sulfoxide products with high activity in a one-pot reaction.
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