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TEMPO‐Catalyzed Aerobic Oxidative Coupling of Thiols for Metal‐Free Formation of S−N/S−S Bonds

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The catalytic synthesis of organic sulfenamides and disulfides has great significance and value in synthetic chemistry and bioscience. To establish a versatile and efficient technology for such reactions, we successfully… Click to show full abstract

The catalytic synthesis of organic sulfenamides and disulfides has great significance and value in synthetic chemistry and bioscience. To establish a versatile and efficient technology for such reactions, we successfully developed a new aerobic oxidative coupling method to construct S-N/S-S bonds, which uses TEMPO as the catalyst, and O2 as the oxidant. A variety of amines and thiols were well tolerated. Sulfenamides were produced in up to 99% yield while disulfides were formed in up to 97% yield in one-pot synthesis. The activation of N-H bond by 2,2-disbenzothiazoledisulfide showed the great potential in organic synthesis.

Keywords: chemistry; aerobic oxidative; oxidative coupling; tempo catalyzed; coupling thiols; catalyzed aerobic

Journal Title: Asian Journal of Organic Chemistry
Year Published: 2017

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