Cu-catalyzed one-pot synthesis of unsymmetrical diaryl thioethers by coupling of aryl halides using a thiol precursor
- PMID: 21271689
- DOI: 10.1021/ol103041s
Cu-catalyzed one-pot synthesis of unsymmetrical diaryl thioethers by coupling of aryl halides using a thiol precursor
Abstract
An efficient Cu-catalyzed one-pot approach for the synthesis of unsymmetrical diaryl thioethers using potassium ethyl xanthogenate as a thiol surrogate is developed. This new protocol avoids usage of intricate thiols and makes use of its easily available xanthate as a precursor, and thiol will be generated in situ to prepare the diaryl thioethers through a Cu-catalyzed double arylation. This strategy was further successfully utilized for the synthesis of symmetrical diaryl thioethers, aryl alkyl thioethers, and benzothiazoles.
Similar articles
-
Cu-catalyzed in situ generation of thiol using xanthate as a thiol surrogate for the one-pot synthesis of benzothiazoles and benzothiophenes.Org Biomol Chem. 2013 Feb 13;11(10):1659-65. doi: 10.1039/c3ob26915a. Org Biomol Chem. 2013. PMID: 23358646
-
Efficient iron/copper cocatalyzed S-arylations of thiols with aryl halides.J Comb Chem. 2009 May-Jun;11(3):338-40. doi: 10.1021/cc800182q. J Comb Chem. 2009. PMID: 19260652
-
Transition-metal-free acid-mediated synthesis of aryl sulfides from thiols and thioethers.J Org Chem. 2014 Mar 7;79(5):2263-7. doi: 10.1021/jo402567b. Epub 2014 Feb 19. J Org Chem. 2014. PMID: 24548014
-
Transition-metal-catalyzed C-S bond coupling reaction.Chem Asian J. 2014 Mar;9(3):706-22. doi: 10.1002/asia.201301500. Epub 2014 Jan 17. Chem Asian J. 2014. PMID: 24443103 Review.
-
[Development of a General Synthetic Method for Organoselenium Compounds Utilizing Copper Catalyzed Cross Coupling and C-H Bond Activation].Yakugaku Zasshi. 2020;140(9):1101-1106. doi: 10.1248/yakushi.20-00112. Yakugaku Zasshi. 2020. PMID: 32879242 Review. Japanese.
Cited by
-
Metal-free photo-induced sulfidation of aryl iodide and other chalcogenation.Front Chem. 2022 Jul 26;10:941016. doi: 10.3389/fchem.2022.941016. eCollection 2022. Front Chem. 2022. PMID: 35958235 Free PMC article.
-
The reaction of potassium xanthates with five-membered cyclic carbonates: selectivity of the underlying cascade reactions and mechanistic insights.RSC Adv. 2020 Oct 1;10(60):36303-36316. doi: 10.1039/d0ra07428d. eCollection 2020 Oct 1. RSC Adv. 2020. PMID: 35517935 Free PMC article.
-
Silver-catalyzed direct thiolation of quinones by activation of aryl disulfides to synthesize quinonyl aryl thioethers.J Org Chem. 2015 May 15;80(10):4919-27. doi: 10.1021/acs.joc.5b00247. Epub 2015 Apr 27. J Org Chem. 2015. PMID: 25894360 Free PMC article.
-
Synthetic exploration of electrophilic xanthylation via powerful N-xanthylphthalimides.Chem Sci. 2023 Aug 1;14(34):9197-9206. doi: 10.1039/d3sc03194b. eCollection 2023 Aug 30. Chem Sci. 2023. PMID: 37655020 Free PMC article.
-
Efficient Cu-catalyzed base-free C-S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides.Beilstein J Org Chem. 2013;9:467-75. doi: 10.3762/bjoc.9.50. Epub 2013 Mar 4. Beilstein J Org Chem. 2013. PMID: 23503063 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources