Reductive decarboxylation of N-(acyloxy)phthalimides via redox-initiated radical chain mechanism

Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis

“…In an early contribution, Okada and co-workers demonstrated in 1991 that N -(acyloxy)phthalimides may be used as a masking group for alkyl radicals. 64 Employing the familiar reductive quenching pathway, 1-benzyl-1,4-dihydronicotinamide (BNAH, 1 ) quenches *Ru(bpy) 3 2+ to give Ru(bpy) 3 + and the BNAH radical cation ( 4 ) (Scheme 19). Single-electron reduction of N -(acyloxy)phthalimide 68 by Ru(bpy) 3 + proceeds to give radical anion 69 , which upon protonation fragments to give phthalimide, carbon dioxide, and alkyl radical 70 .…”

Synthesis of Elongated Esters from Alkenes

“…An experiment using 793 milligrams of 1a (6.0 mmol) and 4.09 grams of 9b (12 mmol) gave ac omparable result to yield 1.13 grams of 10 b,i ndicating the scalability of the present reaction (entry 3). Carbodiimide-mediated condensation with N-hydroxyphthalimide (NHPI) afforded the ester 12.T he following reductive photodecarboxylation [19] afforded 1-phenylpentane (13). Ther eaction with the gbutyrolactone phosphorus ylide 9e was slower (entry 6).…”

Photoredox catalysis by [Ru(bpy)3]2+ to trigger transformations of organic molecules. Organic synthesis using visible-light photocatalysis and its 20th century roots

“…In a related work, the key alkyl radical intermediates 54 generated as depicted in Scheme 19 can give rise to reduced species R-H when t-BuSH reagent is used as a source of the hydrogen atom 39 . Alternatively the alkyl radicals 54 can be trapped with PhSeSePh to give phenyl selenides R-SePh 40 .…”