Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides.
J Am Chem Soc
; 140(51): 17878-17883, 2018 12 26.
Article
in En
| MEDLINE
| ID: mdl-30525575
ABSTRACT
A nickel-catalyzed conjunctive cross-coupling of simple alkenyl amides with aryl iodides and aryl boronic esters is reported. The reaction is enabled by an electron-deficient olefin (EDO) ligand, dimethyl fumarate, and delivers the desired 1,2-diarylated products with excellent regiocontrol. Under optimized conditions, a wide range of amides derived from 3-butenoic acid, 4-pentenoic acid, and allyl amine are compatible substrates. This method represents the first example of regiocontrolled 1,2-diarylation directed by a native amide functional group. Computational analysis sheds light on the potential substrate binding mode and the role of the EDO ligand in the reductive elimination step.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Boronic Acids
/
Alkenes
/
Coordination Complexes
/
Amides
/
Iodobenzenes
/
Nickel
Language:
En
Journal:
J Am Chem Soc
Year:
2018
Type:
Article
Affiliation country:
United States