411208-03-2Relevant articles and documents
Tridentate Nickel(II)-Catalyzed Chemodivergent C-H Functionalization and Cyclopropanation: Regioselective and Diastereoselective Access to Substituted Aromatic Heterocycles
Nag, Ekta,Gorantla, Sai Manoj N. V. T.,Arumugam, Selvakumar,Kulkarni, Aditya,Mondal, Kartik Chandra,Roy, Sudipta
supporting information, p. 6313 - 6318 (2020/09/02)
A Schiff-base nickel(II)-phosphene-catalyzed chemodivergent C-H functionalization and cyclopropanation of aromatic heterocycles is reported in moderate to excellent yields and very good regioselectivity and diastereoselectivity. The weak, noncovalent interaction between the phosphene ligand and Ni center facilitates the ligand dissociation, generating the electronically and coordinatively unsaturated active catalyst. The proposed mechanisms for the reported reactions are in good accord with the experimental results and theoretical calculations, providing a suitable model of stereocontrol for the cyclopropanation reaction.
Synthesis of Cyclopropanated 7-Azabenzonorbornadienes
Carlson, Emily,Tam, William
, p. 2449 - 2454 (2016/07/28)
7-Azabenzonorbornadienes bearing various aryl or N-substituents were treated with diazomethane in the presence of palladium to afford desirable yields of cyclopropanated products (75-98%). The current approach suggests an efficient synthesis for CH2-cyclopropanated 7-azabenzonorbornadienes which lends promise to the development of new ring-opening preparations of biologically useful organic frameworks.
Elements of regiocontrol in palladium-catalyzed oxidative arene cross-coupling
Stuart, David R.,Villemure, Elisia,Fagnou, Keith
, p. 12072 - 12073 (2008/03/27)
By changing the stoichiometric oxidant and modifying the indole N-substituent in palladium-catalyzed oxidative arene cross-coupling reactions, both C2 and C3 oxidative indole arylation can be achieved in high yield. High regioselectivity can also be achieved with the benzene component, and the use of this methodology with pyrrole substrates is illustrated. A mechanistic hypothesis for the change in C2/C3 selectivity is advanced. Copyright
Development of two processes for the synthesis of bridged azabicyclic systems: Intermolecular radical addition-homoallylic rearrangements leading to 2-azanorborn-5-enes and neophyl-type radical rearrangements to 2-azabenzonorbornanes
Hodgson, David M.,Bebbington, Magnus W.P.,Willis, Paul
, p. 3787 - 3798 (2007/10/03)
Radical thiol additions to 7-azanorbornadienes give 7-thio-substituted 2-azanorbornenes and Barton deoxygenations of 7-azabenzonorbornanols give 2-azabenzonorbornanes. The processes both involve novel nitrogen-directed radical rearrangements. The kinetics and mechanisms of the reactions are also discussed.
