Palladium‐Catalyzed Reaction of Aryl Iodides and Glycal Enones: Application in the Preparation of Dapagliflozin Analogues

An efficient approach for the preparation of C‐1 aryl enones from aryl iodides and glycal enones by palladium‐catalyzed cross‐coupling reactions under ligand‐free conditions was developed. A wide range of aryl iodides bearing electron‐donating and withdrawing groups underwent oxidative C‐1 arylation...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-09, Vol.2022 (33), p.n/a
Main Authors: Kumar Singh, Adesh, Venkatesh, Rapelly, Kumar Kanaujiya, Vimlesh, Tiwari, Varsha, Kandasamy, Jeyakumar
Format: Article
Language:English
Subjects:
Aromatic compounds
Aryl Iodides
Aryl-C-glycosides
Chemical reactions
Cross coupling
Dapagliflozin
Iodides
Nitration
Palladium
Silver nitrate
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Summary:An efficient approach for the preparation of C‐1 aryl enones from aryl iodides and glycal enones by palladium‐catalyzed cross‐coupling reactions under ligand‐free conditions was developed. A wide range of aryl iodides bearing electron‐donating and withdrawing groups underwent oxidative C‐1 arylation with galactal, glucal and rhamnal enones in the presence of Pd(OAc)2 and AgNO3 under mild conditions. The protecting groups, including benzyl, acetyl, pivaloyl, and benzoyl groups, were found to be compatible under standard reaction conditions. The developed methodology was applied for the preparation of dapagliflozin analogues (SGLT‐2 inhibitors). Regioselective nitration of C‐1 aryl enones provides C‐2 nitro aryl enones in good yields. A wide range of aryl iodides bearing electron‐donating and withdrawing groups underwent oxidative C‐1 arylation with enones derived from glycals in the presence of Pd(OAc)2 and AgNO3 under ligand‐free conditions. The developed methodology was successfully applied in the preparation of dapagliflozin analogues (SGLT‐2 inhibitor).
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200023