Ruthenium-catalyzed cyclocarbonylation of aliphatic amides through the regioselective activation of unactivated C(sp3)–H bonds

Pd-Catalyzed C(sp3)–H Carbonylation of Alkylamines: A Powerful Route to γ-Lactams and γ-Amino Acids

“…The carbonylation of 2-pyridyl-protected alkylamines with a quaternary β-carbon atom proceeded smoothly to afford the corresponding pyrrolidones in good to excellent yields (2b−c, Scheme 2). While substrates containing a hydrogen atom at the carbon atom adjacent to the reaction site showed lower reactivity in the reported methods, 7,8 protected alkylamines bearing only one (2d−f) or even no β-alkyl group (2g−i) were well tolerated in our catalytic system without any decline of catalytic activity. Notably, n-propylamine derivative 1j was also well tolerated to give pyrrolidone 2j in good yield (82%).…”

Copper‐Catalyzed Site‐Selective Intramolecular Amidation of Unactivated C(sp3)H Bonds

“…[5] Furthermore, ironcatalyzed direct arylation and alkylation reaction of sp 3 carbon atoms was also demonstrated by Nakamura and coworkers. [6] Very recently, nickel-catalyzed site-selective alkylation of unactivated sp 3 CÀH bonds was established in our laboratory.…”

Catalytic C–H Bond Functionalization of Cyclopropane Derivatives

“…After an amide-directed Pd activation of the cyclopropyl C-H bond of 18, a migratory insertion of CO takes place, and the subsequent Pd intermediate undergoes C-N reductive elimination to provide a succinimide product 19 in 86% yield (Scheme 3b). More recently, Chatani demonstrated cyclopropyl carbonylation in the presence of an N,N-bidentate group under Ru 3 (CO) 12 catalysis [23].…”