α-Diimine-mediated C-H functionalization of arenes for aryl-aryl cross-coupling reactions.
Org Biomol Chem
; 22(12): 2389-2394, 2024 Mar 20.
Article
in En
| MEDLINE
| ID: mdl-38329231
ABSTRACT
Easily accessible methods for direct C-H arylation of arenes have been explored in the presence of transition metal catalysts to facilitate C-C bond formation; however, the absence of transition-metal impurities is a significant concern in the preparation of active pharmaceutical ingredients (APIs). Herein, we examine the use of bis(imino)acenaphthene (BIAN) as a potential single-electron transfer initiator in transition metal-free C-C bond-forming reactions. Using this approach, arenes are coupled to several aryl and heteroaryl halides. Based upon preliminary mechanistic evidence and crystallographic probation of an active initiator species, we tentatively propose a potassium-stabilized 'metal-free' radical pathway is in operation.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Org Biomol Chem
Journal subject:
BIOQUIMICA
/
QUIMICA
Year:
2024
Document type:
Article
Affiliation country:
United States
Country of publication:
United kingdom