Palladium(II)-Catalyzed Mono- and Bis-alkenylation of N-Acetyl-2-aminobiaryls through Regioselective C–H Bond Activation

Abstract

We developed palladium-catalyzed oxidative coupling of olefins with N-acyl 2-aminobiaryls through a sequence of ortho C-H bond activation/alkene insertion/reductive elimination. Furthermore, we controlled the selectivity of mono- and bis-alkenylation products with the solvent effect. The developed protocol was promising for a broad substrate scope ranging from activated olefins with a wide variety of functional groups to unactivated olefins.

Aromás vegyületek regioszelektív funkcionalizálása nemszimmetrikus jodóniumsók felhasználásával

“…Ezt kihasználva, kiterjesztették a reakciót N-([1,1'-bifenil]-2-il)acetamidok mono-és dialkenilezésére is. 306 38. ábra. Közvetlen palládiumkatalizált C-H alkenilezési reakciók különböző irányító csoport jelenlétében.…”

Ligand-free Pd-catalyzed highly selective arylation of activated and unactivated alkenes via oxidative and reductive heck coupling

“…2 Attempts to overcome these drawbacks include attempted syntheses of efficient catalysts; 3 the utilization of solvent-free reaction conditions; and the application of non-classical energy sources such as microwave irradiation, high pressure, and mechanochemical techniques. 4 Despite significant advances in acyclic aliphatic alkenes and cycloenones (Scheme 1A), 5 a – d the synthesis of cyclic olefins involving oxidative or reductive Heck coupling continues to be particularly challenging. Additionally, chemo-selectivity is another commonly faced problem within directing-group-assisted C–H olefination.…”

“…Additionally, chemo-selectivity is another commonly faced problem within directing-group-assisted C–H olefination. 5 Hence, it is of great synthetic value to develop a practical methodology to address these long-standing issues.…”

Distal-C–H Functionalization of Biphenyl Scaffolds Assisted by Easily Removable/Recyclable Aliphatic Nitrile Templates

“…Biaryls are favored structural motifs in various natural products, biologically active substances, and active medicinal ingredients. , The o -C–H functionalization of biphenyl systems has been extensively investigated via stable and proximal metallacycles; − however, the intricate m -C–H functionalization of the biphenyls has scarcely been explored. For instance, Maiti et al.…”