4.7 Article

Benzylic C(sp3)-H bond sulfonylation of 4-methylphenols with the insertion of sulfur dioxide under photocatalysis

Journal

CHEMICAL COMMUNICATIONS
Volume 54, Issue 79, Pages 11172-11175

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8cc06567e

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Sulfonylation of the benzylic C-H bond is developed through a three-component reaction of aryldiazonium tetrafluoroborates, 4-methylphenols and sodium metabisulfite (Na2S2O5). The inorganic sulfite of sodium metabisulfite is used as the SO2 surrogate. In this transformation, benzylic C(sp(3))-H bond sulfonylation is achieved in the presence of a photocatalyst under visible light. A radical pathway involving the arylsulfonyl radical and intermolecular hydrogen atom abstraction is proposed.

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