📜4-乙基苯硼酸,2-氯-5-正丙基嘧啶置于四(三苯基膦)钯,Potassium Carbonate体系中,用 乙二醇二甲醚,乙醇 作为反应溶剂,以81 %的收率获得产物5-丙基-2-(4-乙基苯基)嘧啶
参考文献:C(Sp3)-h (N‐phenyltetrazole)Thiolation As An Enabling Tool For Molecular Diversification
标题:C(Sp3)-h (N‐phenyltetrazole)Thiolation As An Enabling Tool For Molecular Diversification
摘要:Methods Enabling The Broad Diversification Of C(Sp3)-h Bonds From A Common Intermediate Are Especially Valuable In Chemical Synthesis. Herein,We Report A Site‐selective (N‐phenyltetrazole)Thiolation Of Aliphatic And (Hetero)Benzylic C(Sp3)-h Bonds Using A Commercially Available Disulfide To Access N‐phenyltetrazole Thioethers. The Thioether Products Are Readily Elaborated In Diverse Fragment Couplings For C-c,C-o,Or C-n Construction. The C-h Functionalization Proceeds Via A Radical‐chain Pathway Involving Hydrogen Atom Transfer By The Electron‐poor N‐phenyltetrazolethiyl Radical. Hexafluoroisopropanol Was Found To Be Essential To Reactions Involving Aliphatic C(Sp3)-h Thiolation,With Computational Analysis Consistent With Dual Hydrogen Bonding Of The N‐phenyltetrazolethiyl Radical Imparting Increased Radical Electrophilicity To Facilitate The Hydrogen Atom Transfer. Substrate Is Limiting Reagent In All Cases,And The Reaction Displays An Exceptional Functional Group Tolerance Well Suited To Applications In Late‐stage Diversification.
DOI:10.1002/anie.202404879