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Abstract
Transition-metal-catalyzed C−H bond activation employing a directing group has been shown to be a powerful tool to access C−C or C−hetero bond formation. Oxygen and nitrogen atoms are commonly applied as the electron donor for these directing groups. In contrast, there are only a few studies on sulfur-containing groups, probably due to their toxicity to transition-metal catalysts. Nowadays, a large amount of C−H activation reactions directed by sulfur-containing auxiliary groups have been successfully achieved. As these groups can be facilely removed or modified in situ or in further steps, they are of great value in creative synthetic strategies. This paper reviews recent advances in the studies using thioether, thiol/thiophenol/disulfide, sulfoxide, and thiocarbonyl as directing groups for intermolecular C−H functionalizations as well as intramolecular oxidative annulations.
Keywords: C−H activation, directing group, sulfur, thioether, disulfide, sulfoxide, thiocarbonyl.
Mini-Reviews in Organic Chemistry
Title:A Review on Sulfur-Directed C−H Bond Activation
Volume: 18 Issue: 7
Author(s): Xuchong Tang and Yingwei Zhao*
Affiliation:
- College of Chemical Engineering, Huaqiao University, 668 Jimei Blvd, Xiamen 361021,China
Keywords: C−H activation, directing group, sulfur, thioether, disulfide, sulfoxide, thiocarbonyl.
Abstract: Transition-metal-catalyzed C−H bond activation employing a directing group has been shown to be a powerful tool to access C−C or C−hetero bond formation. Oxygen and nitrogen atoms are commonly applied as the electron donor for these directing groups. In contrast, there are only a few studies on sulfur-containing groups, probably due to their toxicity to transition-metal catalysts. Nowadays, a large amount of C−H activation reactions directed by sulfur-containing auxiliary groups have been successfully achieved. As these groups can be facilely removed or modified in situ or in further steps, they are of great value in creative synthetic strategies. This paper reviews recent advances in the studies using thioether, thiol/thiophenol/disulfide, sulfoxide, and thiocarbonyl as directing groups for intermolecular C−H functionalizations as well as intramolecular oxidative annulations.
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Cite this article as:
Tang Xuchong and Zhao Yingwei*, A Review on Sulfur-Directed C−H Bond Activation, Mini-Reviews in Organic Chemistry 2021; 18 (7) . https://dx.doi.org/10.2174/1570193X17999201113142442
DOI https://dx.doi.org/10.2174/1570193X17999201113142442 |
Print ISSN 1570-193X |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6298 |
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