1. Syntheses of Selenide Ethers and Thioesters from Methyl Arenes Through sp³ C-H Functionalization2. Peracetic Acid-Mediated sp² C-H Selenation of Methyl Arenes

• Main Authors: Ping- An Hsieh, 謝秉桉
• Other Authors: Chin-Fa Lee
• Format: Others
• Language: zh-TW
• Published: 2015
• Online Access: http://ndltd.ncl.edu.tw/handle/3bg959

碩士 === 國立中興大學 === 化學系所 === 103 === In the first part of this thesis, A DTBP-promoted, operationally simple, metal-free and solvent-free C-Se and C-S bond formation through a sp³ C-H functionalization of methyl arenes with diselenides and disulfides is described. Diselenides and disulfides containing various functionalities were coupled smoothly with a broad spectrum of methyl arenes, afforded the corresponding selenide ethers and thioesters in moderate to good yields. This system shows good functional group tolerance, functional groups including chloro, bromo, trifluoromethyl and iodo were tolerated by the reaction conditions. Methyl heteroaryl compounds also coupled well with both of diselenides and disulfides to provide corrosponding selenide ether and thioester respectively. In the second part of this thesis, AcOOH promoted C-Se coupling reaction of arenes with diselenides under metal free and solvent free conditions has been described. The resulting selenide ethers were obtained in good to excellent yields. Very recently, we have reported a DTBP (di-tert-butyl peroxide) promoted syntheses of selenide ethers from methyl arenes via sp³ C-H functionalization. Now, we have observed an interesting oxidant and herein report the AcOOH mediated sp² C-H selenation of methyl arenes under metal free and solvent free conditions.