Palladium-catalyzed oxidative C-N bond coupling involving a solvent-controlled regioselective bromination process
Stereoselective palladium-catalyzed oxidative C-N bond coupling reactions between aromatic amines and alkenes involving a solvent-controlled regioselective bromination process under 1 atm of oxygen atmosphere are disclosed, providing easy access to two different brominated enamines. The addition of hydrogen peroxide (30% aq) as a co-oxidant in the system is crucial for the dehydrogenative aminohalogenation under molecular oxygen (1 atm), and in such a case, the C-N bond coupling/electrophilic bromination reaction cascade is proposed. Furthermore, the different reaction media leads to a switched regioselectivity of the process.
Ji, Xiaochen,Huang, Huawen,Xiong, Wenfang,Huang, Kunbo,Wu, Wanqing,Jiang, Huanfeng
p. 7005 - 7011
(2014/08/18)
Palladium-catalyzed intermolecular dehydrogenative aminohalogenation of alkenes under molecular oxygen: An approach to brominated enamines
A novel and efficient palladium-catalyzed dehydrogenative aminohalogenation of alkenes with molecular oxygen as the sole oxidant has been developed. This protocol provides a valuable synthetic tool for the assembly of a wide range of brominated enamines under mild conditions, with unprecedented stereoselectivity and exceptional functional group tolerance. This attractive route for the synthesis of brominated enamines is of great significance due to the products' versatile reactivity for further transformations.
Ji, Xiaochen,Huang, Huawen,Wu, Wanqing,Jiang, Huanfeng
supporting information
p. 5286 - 5289
(2013/05/21)
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