Cobalt(II)-Catalyzed Acyloxylation of C–H Bonds in Aromatic Amides with Carboxylic Acids

Abstract

The cobalt(II)-catalyzed acyloxylation of C-H bonds in aromatic amides containing an 8-aminoquinoline moiety as the directing group with carboxylic acids is reported. Various carboxylic acids including aromatic and aliphatic carboxylic acids are applicable to the reaction. The reaction displays a broad substrate scope and high functional group tolerance. The reaction is carried out under air.

Rhodium‐Catalyzed C(sp2)‐ or C(sp3)−H Bond Functionalization Assisted by Removable Directing Groups

“…[171] 6.2.5. [173][174][175][176][177][178][179][180][181][182][183][184][185][186] Theu tility of an 8aminoquinoline moiety for the Rh-catalyzed functionalization of amides discussed here was mainly reported by Chatani and co-workers in terms of various alkylation and alkenylation reactions. [172] Thee ase of installation and removal of the 8- aminoquinoline moiety enhances the utility of its usage in synthetic chemistry and many groups have focused their studies on this directing group.…”

“…[172] Thee ase of installation and removal of the 8- aminoquinoline moiety enhances the utility of its usage in synthetic chemistry and many groups have focused their studies on this directing group. [173][174][175][176][177][178][179][180][181][182][183][184][185][186] Theu tility of an 8aminoquinoline moiety for the Rh-catalyzed functionalization of amides discussed here was mainly reported by Chatani and co-workers in terms of various alkylation and alkenylation reactions. [187][188][189][190][191][192][193] In 2014, the Rh I -catalyzed alkylation of 8-aminoquinoline amides was first reported in the reaction of a,b-unsaturated esters (Scheme 53 a).…”

Cross-dehydrogenative coupling reactions between arenes (C–H) and carboxylic acids (O–H): a straightforward and environmentally benign access to O-aryl esters

“…of Ag 2 CO 3 in DCE under the open air afforded the corresponding mono-acyloxylated N-(quinolin-8-yl)benzamides 54 in relatively low to excellent yields (Scheme 23). 40 This reaction tolerated many functional groups, including uoro, bromo, triuoromethyl, ether, and ester functionalities that offers scope for further transformations on the benzamide ring.…”

Rhodiumkatalysierte sp2‐ und sp3‐C‐H‐Funktionalisierungen mit entfernbaren dirigierenden Gruppen

“…Zu den vielseitigen und zuverlässigen zweizähnigen dirigierenden Gruppen, die bislang erforscht wurden, gehört der 8‐Aminochinolinamid‐Baustein, welcher 2005 von Daugulis bei Pd‐katalysierten C‐H‐Arylierungsreaktionen eingeführt wurde . Der 8‐Aminochinolin‐Baustein kann leicht installiert und wieder entfernt werden, sodass sich viele Arbeitsgruppen auf diese dirigierende Gruppe konzentriert haben . Die hier diskutierte Anwendung des 8‐Aminochinolin‐Bausteins für die Rh‐katalysierte Funktionalisierung von Amiden geht hauptsächlich auf die von Chatani veröffentlichten Alkylierungs‐ und Alkenylierungsreaktionen zurück.…”