Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/87028
Title: Water-promoted C-S bond formation reactions
Authors: Xie, Peizhong
Wang, Jinyu
Liu, Yanan
Fan, Jing
Wo, Xiangyang
Fu, Weishan
Sun, Zuolian
Loh, Teck-Peng
Keywords: Allylic Alcohol
Water
Issue Date: 2018
Source: Xie, P., Wang, J., Liu, Y., Fan, J., Wo, X., Fu, W., et al. (2018). Water-promoted C-S bond formation reactions. Nature Communications, 9(1), 1321-.
Series/Report no.: Nature Communications
Abstract: Allylic sulfones, owning to their widespread distributions in biologically active molecules, received increasing attention in the past few years. However, the synthetic method under mild conditions is still a challenging task. In this paper, we report a sulfinic acids ligation with allylic alcohols via metal-free dehydrative cross-coupling. Both aliphatic and aromatic sulfinic acids react with various allylic alcohols to deliver the desired allylic sulfones in high yields with excellent selectivity. This carbon–sulfur bond formation reaction is highly efficient and practical since it works under metal-free, neutral, aqueous media and at room temperature in which the products even can be obtained by simple filtration without the need for organic extraction or column chromatography. Water is found to be essential for the success of this carbon–sulfur bond formation reaction. DFT calculations imply that water acts as promoter in this transformation via intermolecular hydrogen bonds.
URI: https://hdl.handle.net/10356/87028
http://hdl.handle.net/10220/45303
DOI: 10.1038/s41467-018-03698-8
Rights: © 2018 The Author(s). This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/ licenses/by/4.0/.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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