1291713-01-3Relevant academic research and scientific papers
Cobalt-Catalyzed ortho-C?H Functionalization/Alkyne Annulation of Benzylamine Derivatives: Access to Dihydroisoquinolines
Martínez, ángel Manu,Rodríguez, Nuria,Gómez-Arrayás, Ramón,Carretero, Juan C.
supporting information, p. 11669 - 11676 (2017/08/30)
A practical picolinamide-directed C?H functionalization/alkyne annulation of benzylamine derivatives enabling access to the previously elusive 1,4-dihydroisoquinoline skeleton was developed using molecular O2 as the sole oxidant and Co(OAc)2 as precatalyst. The method is compatible with both internal and terminal alkynes and shows high versatility and functional-group tolerance. Furthermore, full preservation of enantiopurity is observed when using non-racemic α-substituted benzylamine derivatives. Kinetic analysis of the reagents and catalyst, labeling experiments, and the isolation and identification of catalytically competent Co-complexes revealed important insights about the mechanism.
Cobalt-Catalyzed Selective Synthesis of Isoquinolines Using Picolinamide as a Traceless Directing Group
Kuai, Changsheng,Wang, Lianhui,Li, Bobin,Yang, Zhenhui,Cui, Xiuling
supporting information, p. 2102 - 2105 (2017/04/27)
Picolinamide has first been employed as a traceless directing group for the cobalt-catalyzed oxidative annulation of benzylamides with alkynes to synthesize isoquinolines through C-H/N-H bonds activation. Oxygen is used as a terminal oxidant. This protocol exhibits good functional group tolerance and excellent regioselectivity. Both terminal and internal alkynes can be efficiently applied to this catalytic system as substrates.
Palladium-catalyzed picolinamide-directed halogenation of ortho C-H bonds of benzylamine substrates
Lu, Chengxi,Zhang, Shu-Yu,He, Gang,Nack, William A.,Chen, Gong
, p. 4197 - 4203 (2014/06/09)
We report a new set of methods for the halogenation of the ortho C-H bonds of N-benzyl picolinamides under palladium-catalyzed conditions. These reactions feature the use of a unique combination of K(Na)XO3 and K 2S2O
