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Title: Studies on copper-catalyzed aerobic reactions of N-H imines
Authors: Ang, Gim Yean
Keywords: DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Issue Date: 2012
Source: Ang, G. Y. (2012). Studies on copper-catalyzed aerobic reactions of N-H imines. Doctoral thesis, Nanyang Technological University, Singapore.
Abstract: On investigating copper-catalyzed aerobic reactions of N-H imines, it was discovered that the iminyl copper species formed from reaction of Grignard reactions with carbonitriles, could undergo either C-H oxygenation or C-C bond cleavage depending on the starting material. The methylene C-H oxidation provides 1,2-diacylbenzenes, which could be further transformed into phthalazines and isoindolines, while a C-C bond cleavage provides carbonitriles using pivalonitrile as a cyanide source. Both transformations are aided by the oxidation of the iminyl copper species with diradical oxygen to form a peroxycopper intermediate, followed by oxidation or homolytic cleavage to effect oxidation and C-C bond cleavage respectively. Both reactions could provide a range of desired products in respectable yields.
DOI: 10.32657/10356/50839
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Theses

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