Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives

Abstract

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO release with water being the source of protons.

Stacking of Sterically Congested Trifluoromethylated Aromatics in their Crystals – The Role of Weak F···π or F···F Contacts

“…Moreover, there are two conformations of molecule 3 in the crystal‐“C 6 F 5 ‐upwards” and “C 6 F 5 ‐downwards”, which lead to the CF 3 ‐aromatic/pentafluorophenyl/CF 3 ‐aromatic stacking motif (Figure d). On the other hand, analyzing the corresponding crystal structure of N‐benzylbenzamide (CCDC 1577926), the T‐shape π stacking was observed, generated by both CH ··· π and hydrogen bond interactions, instead of the face‐to‐face stacking found in the crystal structure of compound 3 .…”

Transition-Metal-Catalyzed Decarbonylative Functionalization of Phthalimides

“…In 2020, Gramage-Doria et al reported an unexpected protodecarbonylation of phthalimides into amides. 29 These Rucatalyzed decarbonylative transformations were achieved in high yields and shorter reaction time (113)(114)(115)(116)(117)(118)(119)(120)(121)(122)(123)(124). However, selective decarbonylation could not achieve satisfactory results of aromatic ring substituted phthalimide (125-126) (Scheme 23a).…”

Site-Selective Ruthenium-Catalyzed C–H Bond Arylations with Boronic Acids: Exploiting Isoindolinones as a Weak Directing Group

“…We have previously reported improved reaction conditions, and substrate scope and limitations regarding this unexpected ruthenium-catalyzed protodecarbonylation reaction. 24…”