The convenient synthesis and reaction of 2-(arylthio)phenols under ligand-free conditions: arylthioquinone preparation through cascade C–H functionalization and oxidation from arylthiols and aryl iodides. Issue 47 (23rd November 2016)

• Record Type: Journal Article
• Authors: Wang, Dawei; Yu, Xiaoli; Wang, Likui; Yao, Wei; Xu, Zhaojun; Wan, Huida
• Is Part Of: Tetrahedron letters. Volume 57:Issue 47(2016)
• Page Start: 5211
• Page End: 5214
• Publication Date: 2016-11-23
• Subjects: C–H functionalization -- Arylthiols -- Quinone -- 2-(Arylthio)phenols -- Copper; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.10.028
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: An convenient and simple method for copper-catalyzed synthesis of 2-(arylthio)phenols through C–H functionalization of arylthiols and aryl iodides was developed under ligand-free conditions without nitrogen protection. In addition, arylthioquinone derivatives were very easily prepared for one more step of oxidation with moderate to good yields. This provides an alternative and efficient way to 2-(arylthio)phenols and arylthioquinone derivatives smoothly without using ligands and nitrogen protection or expensive arylboronic acids. Highlights: Arylthioquinones synthesis from arylthiols and aryl iodides. Without using ligands and nitrogen protection. Without expensive arylboronic acids. Abstract: A convenient and simple method for copper-catalyzed synthesis of 2-(arylthio)phenols through C–H functionalization of arylthiols and aryl iodides was developed under ligand-free conditions without nitrogen protection. In addition, arylthioquinone derivatives were very easily prepared for one more step of oxidation with moderate to good yields. This provide an alternative and efficient way to 2-(arylthio)phenols and arylthioquinone derivatives smoothly without using ligands and nitrogen protection or expensive arylboronic acids.