Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/89327
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Title: DABCO-promoted diaryl thioether formation by metal-catalyzed coupling of sodium sulfinates and aryl iodides
Authors: Liu, Y 
Lam, LY 
Ye, J 
Blanchard, N
Ma, C 
Issue Date: Jun-2020
Source: Advanced synthesis & catalysis, 15 June 2020, v. 362, no. 12, p. 2326-2331
Abstract: A scalable catalytic synthesis method using commodity chemicals for constructing diaryl thioethers directly from sodium arylsulfinates and iodoarenes is reported in this study. In the presence of CuO or other copper salts such as Cu(OAc)2 as well as palladium catalysts, DABCO demonstrated to be essential to promote this transformation. Various iodoarenes and aryl sulfinates were examined and demonstrated the viability of this method. The mechanistic study showed that radical reactions occurred, while DABCO N-oxide radical can be observed by mass spectrometry. A plausible catalytic mechanism involving DABCO is also discussed, suggesting synergistic reduction of sulfinate by Cu(II) and DABCO is the key step of this coupling reaction.
Keywords: Catalysis
Cross-coupling
DABCO
Radical reactions
Thioethers
Publisher: Wiley-VCH
Journal: Advanced synthesis & catalysis 
ISSN: 1615-4150
EISSN: 1615-4169
DOI: 10.1002/adsc.202000221
Rights: © 2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
This is the peer reviewed version of the following article: Y. Liu, L. Y. Lam, J. Ye, N. Blanchard, C. Ma (2020). DABCO‐promoted Diaryl Thioether Formation by Metal‐catalyzed Coupling of Sodium Sulfinates and Aryl Iodides. Adv. Synth. Catal. 362 (12), 2326-2331, which has been published in final form at https://doi.org/10.1002/adsc.202000221. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
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