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.
Highlights
Allylic sulfones, owning to their widespread distributions in biologically active molecules, received increasing attention in the past few years
The development of atom economical organic reactions that can be carried out under metal-free, neutral, in aqueous media, and at room temperature in which the products can be obtained after the reaction by simple filtration without the need for organic extraction or column chromatography is one of the ultimate goals in organic synthesis
In our continuing effort to develop green processes, we focus on the development of an efficient and practical method for the synthesis of sulfones since they play a prominent role in organic synthesis and exist widely in many bioactive natural products as well as some of the best-selling pharmaceuticals[1] (such as Eletriptan ([2H]-SB-3CT) for the treatment of migraine headache and MMP-2, MMP-9 inhibitor[2] for the treatment of prostate cancer)
Summary
Allylic sulfones, owning to their widespread distributions in biologically active molecules, received increasing attention in the past few years. 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. With our continuing interest in green chemistry[24,25,26] and developing new bioconjugation method for cysteine[27], we embarked on developing an effective metal-free ligation reaction that selectively converts sulfinic acid moieties into allylic sulfones in aqueous media at room temperature under physiological pH This process offers easy access to allylic sulfones in a green manner and shed light on protein sulfinylation detection, including nitrile hydratase, matrilysin, and Parkinson’s disease protein DJ-128, 29
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
