Metal-free insertion of sulfur dioxide with aryl iodides under ultraviolet irradiation: direct access to sulfonated cyclic compounds
Literature Information
Publication Date
2019-11-06
DOI
10.1039/C9QO01274E
Impact Factor
5.281
Authors
Shengqing Ye, Kaida Zhou, Pornchai Rojsitthisak
View Original
Abstract
Metal-free insertion of sulfur dioxide with aryl iodides and silyl enolates or allylic bromide under ultraviolet irradiation at room temperature is accomplished. This protocol provides a convenient route to sulfonated cyclic compounds under mild conditions. Not only N-(2-iodophenyl)-N-methylmethacrylamides but also 1-iodo-2-allenoxybenzene is workable. A plausible mechanism is proposed, which shows that during the reaction process, aryl radicals formed in situ from aryl iodides under ultraviolet irradiation undergo intramolecular 5-exo-cyclization, with subsequent sulfonylation via insertion of sulfur dioxide. The resulting sulfonyl radicals are further trapped by silyl enolates or allylic bromide giving rise to sulfonated cyclic compounds.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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CAS Number:
4162-45-2
Molecular Formula:
C19H20Br4O4
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2,9-Dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione
CAS Number:
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Molecular Formula:
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