title: Direct reductive coupling of secondary amides: chemoselective formation of vicinal diamines and vicinal amino alcohols.
abstract: We report the first one-pot reductive homocoupling reaction of secondary amides and cross-coupling reaction of secondary amides with ketones to give secondary vicinal diamines and amino alcohols. This method relies on the direct generation of α-amino carbon radicals from secondary amides by activation with trifluoromethanesulfonic anhydride, partial reduction with triethylsilane and samarium diiodide-mediated single-electron transfer. The reactions were run under mild conditions and tolerated several functional groups.
authors.affiliation: Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, Collaborative Innovation Centre of Chemistry for Energy Materials, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China. pqhuang@xmu.edu.cn.
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
authors.forename: Qi-Wei
authors.initials: QW
authors.lastname: Lang
authors.forename: Ai-E
authors.initials: AE
authors.lastname: Wang
authors.forename: Jian-Feng
authors.initials: JF
authors.lastname: Zheng
mesh_terms: D000577:Amides / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000577:Amides; D000605:Amino Alcohols; D003959:Diamines