Regioselective Synthesis of Dibenzo[ b , f ]azepin-1-ones via Silver-Catalyzed 7 - endo-dig Cyclization of Alkynyl-Containing Enaminones
Abstract
Regioselective synthesis of multisubstituted dibenzo[ b, f ]azepin-1-ones is achieved though CF 3 CO 2 Ag-catalyzed 7-endo-dig cyclization of terminal alkynes or unactivated internal ones using air as a “green” oxidant. The 100% atom-economical transformation allows the construction of a series of structurally diverse 2,3,4,5-tetrahydro-1 H -dibenzo[ b, f ]azepin-1-ones with 52–89% yields, featuring excellent functional group tolerance and straightforward separation and purification pathways. Also to note, control experiments were conducted to gain crucial insights into the single electron transfer process, where silver(I) functions as the catalyst and molecular oxygen (O 2 ) serves as the benign terminal oxidant.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Catalytic Alkyne Reactions
Synthesis and Characterization of Pyrroles
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 2
- Pages
- 1177–1187
- Publication date
- 2 January 2026
- Language
- EN