Citation: Jing-Jing Ai, Jian Li, Shun-Jun Ji, Shun-Yi Wang. One-pot two-step reaction of selenosulfonate with isocyanides and allyl alcohol under aqueous conditions: Atom-economic synthesis of selenocarbamates and allyl sulfones[J]. Chinese Chemical Letters, ;2021, 32(2): 721-724. doi: 10.1016/j.cclet.2020.07.007 shu

One-pot two-step reaction of selenosulfonate with isocyanides and allyl alcohol under aqueous conditions: Atom-economic synthesis of selenocarbamates and allyl sulfones

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China

shunyi@suda.edu.cn

Received Date: 3 June 2020
Revised Date: 17 June 2020
Accepted Date: 4 July 2020
Available Online: 4 July 2020

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In many reactions involving selenosulfonate or thiosulfonate, the sulfone group often leaves in form of benzenesulfinic acid or sodium benzenesulfinate. A one-pot two-step reaction of selenosulfonate with isocyanides and allyl alcohol under aqueous conditions to afford selenocarbamates and allyl sulfone compounds is reported. The sulfinic acid as the first-step side product is converted to the allyl sulfone compound by water promoted reaction with allyl alcohol. Water acts as both an oxygen source of selenocarbamates and as a promoter to drive the second step reaction. The reactions have the advantages of mild conditions, green, environment-friendly, and high atomic economy.
- Aqueous conditions,
- One-pot two-step process,
- Benzenesulfinic acid,
- Selenocarbamate,
- Allyl sulfone compound
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