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A highly efficient strategy for the direct thiolation of phenols under transition metal-free and solvent-free conditions has been developed. These reactions are operationally simple with employing air (molecular oxygen) as an ideal oxidant and can selectively provide mono- and dithiolation products in good to excellent yields under basic conditions. The reaction tolerates a broad range of aryl thiols and arenes and is especially applicable for large-scale synthesis.
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http://dx.doi.org/10.1021/acs.joc.1c00898 | DOI Listing |
J Org Chem
August 2021
National Engineering Research Center of Pesticide (Tianjin), State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
A highly efficient strategy for the direct thiolation of phenols under transition metal-free and solvent-free conditions has been developed. These reactions are operationally simple with employing air (molecular oxygen) as an ideal oxidant and can selectively provide mono- and dithiolation products in good to excellent yields under basic conditions. The reaction tolerates a broad range of aryl thiols and arenes and is especially applicable for large-scale synthesis.
View Article and Find Full Text PDFJ Org Chem
August 2019
School of Pharmacy , Lanzhou University, West Donggang Road No. 199 , Lanzhou 730000 , China.
A versatile protocol for the direct thiolation of an inert sp C-H bond is presented via a catalytic amount of copper catalysis, by switching related Brønsted bases and regulating the reaction time, and the corresponding mono- and dithiolation products can be obtained selectively in moderate to good yields. The reaction exhibits a relatively broad substrate scope and a good functional group tolerance, even with different heterocyclic amides and alkyl thiols.
View Article and Find Full Text PDFOrg Lett
June 2018
School of Chemistry and Chemical Engineering , Guangdong Pharmaceutical University, Zhongshan 528458 , P. R. China.
An efficient transition-metal-free regioselective C-H/S-H cross-coupling of indolizines with thiols has been developed for the first time to describe a workable route to indolizine thioethers. This finding provides a new method and more straightforward pathway for controllable synthesis of mono- or dithiolation indolizines that are otherwise difficult to obtain by the literature methods. The reaction exhibits good functional group tolerance and high efficiency and affords the products in good to excellent yields.
View Article and Find Full Text PDFChemistry
January 2014
Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203 (PR China).
The rhodium-catalyzed intermolecular direct C-H thiolation of arenes with aryl and alkyl disulfides was developed for the first time to provide a convenient route to aryl thioethers. This strategy is compatible with many different directing groups and exhibits excellent functional group tolerance. More significantly, mono- or dithiolation can be selectively achieved, thus providing a straightforward way for selective preparation of aryl thioethers and dithioethers.
View Article and Find Full Text PDF