Iron-catalysed hydroalumination of internal alkynes

Citations Over TimeTop 12% of 2022 papers

Abstract

Although research on iron-catalysed reactions has recently achieved significant progress, the activity and selectivity of iron catalysts are generally inferior to those of noble-metal catalysts. The development of new iron-catalysed reactions, especially those in which iron catalysts exhibit superior activity or selectivity to other catalysts, is the key to promote iron catalysis. Herein, we report the first protocol for iron-catalysed hydroalumination of internal alkynes. Specifically, in the presence of iron catalysts bearing 2,9-diaryl-1,10-phenanthroline ligands, internal alkynes were stereo- and regioselectively hydroaluminated with the commercially available reagent diisobutylaluminum hydride. Compared with other metal-catalysed alkyne hydroalumination reactions reported in the literature, the iron-catalysed protocol has the following advantages: unusual amino-group-directed regioselectivity, a wide substrate scope, good functional group tolerance, high selectivity, and mild reaction conditions. The alkenylaluminum products prepared in this way could undergo a diverse array of transformations, and were used for the synthesis of bioactive compounds. The current study expands the scope of iron catalysis, provides a new efficient access to alkenylaluminum, discloses the origin of the superiority of iron catalysts, and thus may inspire further studies in related fields.

Related Papers

• → Recent Advances in the Regioselective Synthesis of Pyrazoles(2011)73 cited
• → Stabilization and activation of dienolates with germanium and tin. Stereo- and regioselective aldol reactions, regioselective coupling reactions, and regioselective synthesis of amino acid derivatives(1990)66 cited
• → N-CHLORO-2,3,4,4,5,6-HEXACHLOROCYCLOHEXA- 2,5-DIENYLIDENEAMINE AS A MILD AND HIGHLY REGIOSELECTIVE CHLORINATING REAGENT(2002)5 cited
• → β-Aminoenones in the regioselective synthesis of 1,3,5-trialkylpyrazoles. The influence of the substituents in the mechanism and the regioselectivity of the reaction(1998)12 cited
• → Regioselective Synthesis of 2-Substituted-4-Methylbenzimidazole Nucleosides(2005)2 cited