Facile synthesis of 2-(phenylthio)phenols by copper(I)-catalyzed tandem transformation of C-S coupling/C-H functionalization
- PMID: 20958071
- DOI: 10.1021/ja107758d
Facile synthesis of 2-(phenylthio)phenols by copper(I)-catalyzed tandem transformation of C-S coupling/C-H functionalization
Erratum in
- J Am Chem Soc. 2011 Jan 19;133(2):387
Abstract
2-(Phenylthio)phenols were successfully synthesized from simple phenols and aromatic halides by using dimethyl sulfoxide as the oxidant. The transformation was accomplished via tandem copper(I)-catalyzed C-S coupling/C-H functionalization employing the CuI/L [L = (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one] catalyst system. The mechanism of the reaction was elucidated based on an isotope labeling strategy.
Similar articles
-
Tandem reactions initiated by copper-catalyzed cross-coupling: a new strategy towards heterocycle synthesis.Org Biomol Chem. 2011 Oct 21;9(20):6873-94. doi: 10.1039/c1ob05769c. Epub 2011 Aug 30. Org Biomol Chem. 2011. PMID: 21879127
-
Direct synthesis of enaminone functionalized biaryl ethers by CuI-catalyzed O-arylation of enaminone functionalized phenols.Org Biomol Chem. 2011 Oct 7;9(19):6481-3. doi: 10.1039/c1ob05947e. Epub 2011 Aug 5. Org Biomol Chem. 2011. PMID: 21822515
-
Synthesis of phenothiazines via ligand-free CuI-catalyzed cascade C-S and C-N coupling of aryl ortho-dihalides and ortho-aminobenzenethiols.Chem Commun (Camb). 2012 May 28;48(43):5367-9. doi: 10.1039/c2cc30814b. Epub 2012 Apr 23. Chem Commun (Camb). 2012. PMID: 22525793
-
Copper Catalyzed C-H Activation.Chem Rec. 2019 Jul;19(7):1302-1318. doi: 10.1002/tcr.201800107. Epub 2018 Oct 30. Chem Rec. 2019. PMID: 30375153 Review.
-
Recent advances in copper-catalyzed dehydrogenative functionalization via a single electron transfer (SET) process.Chem Soc Rev. 2012 May 7;41(9):3464-84. doi: 10.1039/c2cs15323h. Epub 2012 Feb 20. Chem Soc Rev. 2012. PMID: 22349590 Review.
Cited by
-
A nickel-catalyzed tandem reaction involving cyclic esterification/C-S bond formation for synthesizing 5-oxa-11-thia-benzofluoren-6-ones.RSC Adv. 2020 Jul 14;10(44):26414-26417. doi: 10.1039/d0ra04367b. eCollection 2020 Jul 9. RSC Adv. 2020. PMID: 35519763 Free PMC article.
-
Copper-catalyzed etherification of arene C-H bonds.Org Lett. 2013 Nov 15;15(22):5842-5. doi: 10.1021/ol402904d. Epub 2013 Nov 1. Org Lett. 2013. PMID: 24180517 Free PMC article.
-
An efficient and mild oxidative approach from thiols to sulfonyl derivatives with DMSO/HBr.Chem Sci. 2023 Nov 1;14(45):13228-13234. doi: 10.1039/d3sc04945k. eCollection 2023 Nov 22. Chem Sci. 2023. PMID: 38023524 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.
-
Copper-catalyzed C-S direct cross-coupling of thiols with 5-arylpenta-2,4-dienoic acid ethyl ester.RSC Adv. 2018 Jul 27;8(47):26828-26836. doi: 10.1039/c8ra05311a. eCollection 2018 Jul 24. RSC Adv. 2018. PMID: 35541071 Free PMC article.
LinkOut - more resources
Full Text Sources
Other Literature Sources
Research Materials