Synthesis of sulfonated naphthols via C-H bond functionalization with the insertion of sulfur dioxide

A three-component reaction of naphthols, sulfur dioxide, and aryldiazonium tetrafluoroborates catalyzed by iron(III) chloride through a radical process via direct C-H functionalization is developed, leading to diverse sulfonated naphthols in good yields. Arylsulfonyl radicals act as the key intermed...

Full description

Saved in:
Bibliographic Details
Published inORGANIC CHEMISTRY FRONTIERS Vol. 5; no. 3; pp. 371 - 375
Main Authors Zhou, Kaida, Chen, Mo, Yao, Liangqing, Wu, Jie
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.02.2018
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Chlorides
Electron transfer
Electrons
Functional groups
Hydrogen bonds
Intermediates
Iron
Iron chlorides
Naphthol
Organic chemistry
Physical Sciences
Science & Technology
Sulfur
Sulfur dioxide
BORONIC ACIDS
REMOVABLE DIRECTING GROUPS
PHENOLS
ONE-POT
3-COMPONENT REACTION
PALLADIUM-CATALYZED AMINOSULFONYLATION
ARYL
ORTHO-ARYLATION
DABSO
MULTICOMPONENT REACTION
Online AccessGet full text

Cover

More Information
Summary:A three-component reaction of naphthols, sulfur dioxide, and aryldiazonium tetrafluoroborates catalyzed by iron(III) chloride through a radical process via direct C-H functionalization is developed, leading to diverse sulfonated naphthols in good yields. Arylsulfonyl radicals act as the key intermediates during the reaction process, and the presence of iron(III) chloride facilitates the formation of a naphthol radical in the reaction through a single electron transfer. Several sensitive functional groups including nitro, halo, cyano, hydroxy, and ester are all compatible under the conditions.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c7qo00811b