Fe(II)-Catalyzed Amination of Aromatic C−H Bonds via Ring Opening of 2<i>H</i>-Azirines: Synthesis of 2,3-Disubstituted Indoles
作者:Samaresh Jana、Mack D. Clements、Barry K. Sharp、Nan Zheng
DOI:10.1021/ol101130e
日期:2010.9.3
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 FeCl2-catalyzed ring opening of 2H-azirines. The method tolerates a variety of functional groups such as Br, F, NO2, OMe, CF3, OTBS, alkenes, and OPiv. The method can also be extended to synthesize azaindoles.
9,10-Dicyanoathracene-sensitized photoreaction of styrylcyclopropanes in the presence of Cu(BF4)2 in MeCN–MeOH gives α-cyclopropyl nenzyl ketones as major products, which are produced via a two-electron oxidation of styrylcyclopropanes followed by a 1,2-migration of the cyclopropyl group.