Dual C(sp<sup>3</sup>)–H and C(sp<sup>2</sup>)–H Activation of 8-Methylquinoline <i>N</i>-Oxides: A Route to Access C7–H Bond
Santu Mandal, Madhab Barman, Bijoy Debnath, Tharmalingam Punniyamurthy
Abstract
A Pd(II)-catalyzed regioselective dual C(sp 3 )–H/C7(sp 2 )–H activation and annulation of 8-methylquinoline N -oxides with maleimide has been accomplished. The use of N -oxide as a weak directing group under Pd(II)-complex catalysis activates the initial C(sp 3 )–H and triggers a relayed, second C7(sp 2 )–H activation. The dual C–H bond activation, [3 + 2]-annulation, facile introduction and removal of the directing group, substrate scope, and functional group diversity are the important practical features.
Topics & Concepts
ChemistryRegioselectivityCatalysisMedicinal chemistryStereochemistryCrystallographyOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques