Accessing Heteroannular Benzoxazole and Benzimidazole Scaffolds via Carbodiimides Using Azide-Isocyanide Cross-Coupling as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived from a Phenothiazine Moiety.
ACS Omega
; 8(12): 11039-11064, 2023 Mar 28.
Article
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| MEDLINE
| ID: mdl-37008148
The coupling of aryl and aliphatic azides with isocyanides yielding carbodiimides (8-17) were efficiently catalyzed by well-defined structurally characterized trans-(MIC)PdI2(L) [MIC = 1-CH2Ph-3-Me-4-(CH2N(C6H4)2S)-1,2,3-triazol-5-ylidene, L = NC5H5 (4), MesNC (5)], trans-(MIC)2PdI2 (6), and cis-(MIC)Pd(PPh3)I2 (7) type palladium complexes, which incidentally mark the first instances of the use of mesoionic singlet palladium carbene complexes for the said application. As observed from the product yields, the catalytic activity varied in the order 4 > 5 â¼ 6 > 7 for these complexes. A detailed mechanistic studies indicated that the catalysis proceeded via a palladium(0) (4a-7 a) species. Using a representative palladium precatalyst (4), the azide-isocyanide coupling was successfully extended to synthesizing two different bioactive heteroannular benzoxazole (18-22) and benzimidazole (23-27) derivatives, thereby broadening the scope of the catalytic application.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
ACS Omega
Año:
2023
Tipo del documento:
Article
País de afiliación:
India
Pais de publicación:
Estados Unidos