title: Ceric ammonium nitrate (CAN) catalyzed modification of ketones via two C-C bond cleavages with the retention of the oxo-group.
abstract: A simple ceric ammonium nitrate (CAN) catalyzed functionalization of ketones through double C-C bond cleavage strategy has been disclosed. This reaction provides a mild, practical method toward carbamoyl azides, which are versatile intermediates and building blocks in organic synthesis. Based on relevant mechanistic studies, a unique and plausible C-C bond and N-O bond cleavage process is proposed, where the oxyamination intermediate plays an important role in this reaction.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Xue Yuan Road 38, Beijing 100191, China.
authors.forename: Peng
authors.initials: P
authors.lastname: Feng
authors.forename: Xiang
authors.initials: X
authors.lastname: Sun
authors.forename: Yijin
authors.initials: Y
authors.lastname: Su
authors.forename: Xinyao
authors.initials: X
authors.lastname: Li
authors.forename: Li He
authors.initials: LH
authors.lastname: Zhang
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Shi
authors.forename: Ning
authors.initials: N
authors.lastname: Jiao
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D064751:Ammonium Compounds / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D002563:Cerium / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D007097:Imines / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010094:Oxonic Acid
chemical_list: D000447:Aldehydes; D064751:Ammonium Compounds; D001386:Azides; D007097:Imines; D007659:Ketones; D002563:Cerium; C489337:potassium oxonate; D010094:Oxonic Acid; C004653:ceric ammonium nitrate