doi: 10.1039/c1cc15397h.
Epub 2011 Oct 31.
TBHP-mediated oxidative thiolation of an sp3 C-H bond adjacent to a nitrogen atom in an amide
Affiliations
- PMID: 22037478
- DOI: 10.1039/c1cc15397h
Item in Clipboard
TBHP-mediated oxidative thiolation of an sp3 C-H bond adjacent to a nitrogen atom in an amide
Chem Commun (Camb).
.
Abstract
The first example of molecular sieve-promoted TBHP-mediated direct oxidative thiolation of an sp(3) C-H bond adjacent to a nitrogen atom with disulfides under metal-free conditions, which allows for preparation of numerous S,N-containing compounds, is presented. Moreover, diverse benzothiazoles and a fipronil analog can be synthesized through this strategy.
This journal is © The Royal Society of Chemistry 2011
Similar articles
-
KI-catalyzed imidation of sp3 C-H bond adjacent to amide nitrogen atom.Org Biomol Chem. 2012 Oct 21;10(39):7869-71. doi: 10.1039/c2ob26430g. Org Biomol Chem. 2012. PMID: 22948963
-
Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles.Chem Soc Rev. 2007 Jul;36(7):1069-84. doi: 10.1039/b607547a. Epub 2007 Mar 1. Chem Soc Rev. 2007. PMID: 17576475 Review.
-
Metal-Free Preparation of Cycloalkyl Aryl Sulfides via Di-tert-butyl Peroxide-Promoted Oxidative C(sp3)[BOND]H Bond Thiolation of Cycloalkanes.Adv Synth Catal. 2014 Aug 10;356(11-12):2719-2724. doi: 10.1002/adsc.201400032. Adv Synth Catal. 2014. PMID: 25505857 Free PMC article.
-
Iron(II)-catalyzed oxidation of sp3 C-H bonds adjacent to a nitrogen atom of unprotected arylureas with tert-butyl hydroperoxide in water.Org Lett. 2011 Apr 1;13(7):1674-7. doi: 10.1021/ol200169g. Epub 2011 Mar 4. Org Lett. 2011. PMID: 21375293
-
Thiolation and nitrosation of cysteines in biological fluids and cells.Amino Acids. 2003 Dec;25(3-4):323-39. doi: 10.1007/s00726-003-0020-1. Epub 2003 Aug 21. Amino Acids. 2003. PMID: 14661094 Review.
Cited by
-
Heterogeneous Catalytic Oxidation of Amides to Imides by Manganese Oxides.Sci Rep. 2018 Sep 11;8(1):13649. doi: 10.1038/s41598-018-31729-3. Sci Rep. 2018. PMID: 30206248 Free PMC article.
-
Catalyst-free reductive cyclization of bis(2-aminophenyl) disulfide with CO2 in the presence of BH3NH3 to synthesize 2-unsubstituted benzothiazole derivatives.RSC Adv. 2022 Jun 20;12(28):18107-18114. doi: 10.1039/d2ra03134e. eCollection 2022 Jun 14. RSC Adv. 2022. PMID: 35800324 Free PMC article.
-
Toward Rational Understandings of α-C-H Functionalization: Energetic Studies of Representative Tertiary Amines.iScience. 2020 Feb 21;23(2):100851. doi: 10.1016/j.isci.2020.100851. Epub 2020 Jan 21. iScience. 2020. PMID: 32058963 Free PMC article.
-
Visible-Light-Driven C-S Bond Formation Based on Electron Donor-Acceptor Excitation and Hydrogen Atom Transfer Combined System.ACS Org Inorg Au. 2021 Jun 22;1(1):23-28. doi: 10.1021/acsorginorgau.1c00007. eCollection 2021 Oct 6. ACS Org Inorg Au. 2021. PMID: 36855634 Free PMC article.
-
Non-Thermal Atmospheric Pressure Plasma Efficiently Promotes the Proliferation of Adipose Tissue-Derived Stem Cells by Activating NO-Response Pathways.Sci Rep. 2016 Dec 19;6:39298. doi: 10.1038/srep39298. Sci Rep. 2016. PMID: 27991548 Free PMC article.
LinkOut - more resources
Full Text Sources
Other Literature Sources
