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Title: Copper-mediated C-H activation/C-S cross-coupling of heterocycles with thiols
Authors: Ranjit, S.
Lee, R.
Heryadi, D.
Shen, C.
Wu, J.
Zhang, P.
Huang, K.-W.
Liu, X. 
Issue Date: 4-Nov-2011
Citation: Ranjit, S., Lee, R., Heryadi, D., Shen, C., Wu, J., Zhang, P., Huang, K.-W., Liu, X. (2011-11-04). Copper-mediated C-H activation/C-S cross-coupling of heterocycles with thiols. Journal of Organic Chemistry 76 (21) : 8999-9007. ScholarBank@NUS Repository.
Abstract: We report the synthesis of a series of aryl- or alkyl-substituted 2-mercaptobenzothiazoles by direct thiolation of benzothiazoles with aryl or alkyl thiols via copper-mediated aerobic C-H bond activation in the presence of stoichiometric CuI, 2,2′-bipyridine and Na 2CO 3. We also show that the approach can be extended to thiazole, benzimidazole, and indole substrates. In addition, we present detailed mechanistic investigations on the Cu(I)-mediated direct thiolation reactions. Both computational studies and experimental results reveal that the copper-thiolate complex [(L)Cu(SR)] (L: nitrogen-based bidentate ligand such as 2,2′-bipyridine; R: aryl or alkyl group) is the first reactive intermediate responsible for the observed organic transformation. Furthermore, our computational studies suggest a stepwise reaction mechanism based on a hydrogen atom abstraction pathway, which is more energetically feasible than many other possible pathways including β-hydride elimination, single electron transfer, hydrogen atom transfer, oxidative addition/reductive elimination, and σ-bond metathesis. © 2011 American Chemical Society.
Source Title: Journal of Organic Chemistry
ISSN: 00223263
DOI: 10.1021/jo2017444
Appears in Collections:Staff Publications

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