Fe(II)-catalyzed amination of aromatic C-H bonds via ring opening of 2H-azirines: synthesis of 2,3-disubstituted indoles.
A general method for the synthesis of 2,3-disubstituted indoles is described. The key feature of this method is the amination of aromatic C-H bonds via FeCl(2)-catalyzed ring opening of 2H-azirines. The method tolerates a variety of functional groups such as Br, F, NO(2), OMe, CF(3), OTBS, alkenes, and OPiv. The method can also be extended to synthesize azaindoles.
Jana
Samaresh
S
Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, USA.
Clements
Mack D
MD
Sharp
Barry K
BK
Zheng
Nan
N
D000586:Amination; D001389:Azirines / Q000737:chemistry*; D002384:Catalysis; D005296:Ferrous Compounds / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D001389:Azirines; D005296:Ferrous Compounds; D007211:Indoles; C029451:ferrous chloride