Water-promoted C-S bond formation reactions

Peizhong Xie (), Jinyu Wang, Yanan Liu, Jing Fan, Xiangyang Wo, Weishan Fu, Zuolian Sun and Teck-Peng Loh ()
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Peizhong Xie: Nanjing Tech University
Jinyu Wang: Nanjing Tech University
Yanan Liu: Nanjing Tech University
Jing Fan: Nanjing Tech University
Xiangyang Wo: Nanjing Tech University
Weishan Fu: Nanjing Tech University
Zuolian Sun: Nanjing Tech University
Teck-Peng Loh: Nanjing Tech University

Nature Communications, 2018, vol. 9, issue 1, 1-8

Abstract: 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.

Date: 2018
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DOI: 10.1038/s41467-018-03698-8

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