A Bu₄N[Fe(CO)₃(NO)]‐Catalyzed Hemetsberger–Knittel Indole Synthesis

Abstract

The nucleophilic Fe complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of aryl vinyl azides to give the corresponding indole derivatives in good to excellent yields.

Telescoped Flow Synthesis of Azacyclic Scaffolds Exploiting the Chromoselective Photolysis of Vinyl Azides and Azirines

“…We initiated our study by preparing a library of vinyl azides from commercially available methyl bromoacetate and benzaldehydes (see ESI for details) [15,16] . Using vinyl azide 1a as the model substrate the formation of 2 H ‐azirines was studied under photochemical conditions.…”

Recent Advances onα‐Azidoketones and Esters in the Synthesis ofN‐Heterocycles

“…). [42] Bu 4 N[Fe(CO) 3 (NO)] was found to act as a nucleophilic catalyst and good to high yields (18-94%) of indoles 60 were obtained by performing the reaction at 80 °C under microwave heating in chloroform.…”

“…Bu 4 N[Fe(CO) 3 (NO)] catalyzed Hemetsberger–Knittel indole synthesis was recently reported by Baykal and Plietker (Scheme 12). [42] Bu 4 N[Fe(CO) 3 (NO)] was found to act as a nucleophilic catalyst and good to high yields (18–94%) of indoles 60 were obtained by performing the reaction at 80 °C under microwave heating in chloroform.…”

Selective oxidation of alcohol-d1 to aldehyde-d1 using MnO2

“…For example, more than 40 syntheses (25 different reaction conditions) of benzaldehyde-d 1 (PhCDO) were conducted even since 2018 in the studies to develop new d-incorporation method or reaction mechanism using PhCDO. [4][5][6][7][8] The previous synthetic approaches to access d-labelled molecules are classied into 5 types; (A) addition of D À followed by oxidation, (B) carbonyl Umpolung approach, (C) radical reaction, (D) transition metal-catalysed reaction, and (E) others. Recently, mild, one-step, and catalytic syntheses of aldehyde-d 1 2 have been achieved by deuteration of the Breslow intermediates, 9 deuteration of acyl radicals, 6,10 and transition metal-catalysed deuterium incorporation.…”