Synthesis of aryl sulfones via L-proline-promoted CuI-catalyzed coupling reaction of aryl halides with sulfinic acid salts.
[reaction: see text] The CuI/L-proline sodium salt catalyzed coupling reaction of aryl halides with sulfinic acid salts readily occurs at 80-95 degrees C in DMSO to give the corresponding aryl sulfones in good to excellent yields. This process is well-tolerated by a wide range of functional groups including hydroxyl, amino, acetanilide, ketone, ester, and nitrile. Using this method, 4-phenylsulfonyl- and 4-methanesulfonyl-substituted L-phenylalanine derivatives are prepared.
Zhu
Wei
W
Department of Chemistry, Fudan University, Shanghai 200433, China.
Ma
Dawei
D
D003300:Copper / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011392:Proline / Q000737:chemistry*; D012492:Salts; D021241:Spectrometry, Mass, Electrospray Ionization; D013441:Sulfinic Acids / Q000737:chemistry*; D013450:Sulfones / Q000138:chemical synthesis*
D006219:Halogens; D007454:Iodides; D012492:Salts; D013441:Sulfinic Acids; D013450:Sulfones; D003300:Copper; C073870:cuprous iodide; D011392:Proline