TMSN3-Bu2Sn(OAc)2: A modified and mild reagent system for Wittenberger tetrazole-synthesis

N‐Fluoromethylated (Amino)Tetrazoles: Manipulating Thermal and Energetic Properties

“…However, until very recently this year, the first and only fluoromethyl containing tetrazole, 5‐fluoromethyl‐tetrazole [ 17 ] and one non‐energetic complex [ 18 ] were reported. Since a large number of fluoromethylating agents for various nucleophiles are available until now [ 19 ] and only N ‐methylated but no N ‐fluoromethylated tetrazoles are known up to date, this prompted us to synthesize fluoromethylated tetrazoles und investigate their thermal‐, energetic‐ and complexation behavior.…”

Enantioselective reaction of N-cyano imines: decarboxylative Mannich-type reaction with malonic acid half thioesters

“…The reaction of imines 1m and 1n bearing electron-donating groups such as methyl and methoxy groups with 2c afforded products 11 and 12, respectively, in high yields and enantioselectivities (Table 2, entries 8 and 9). In addition, high enantioselectivities were obtained in the reactions of 2-naphthylimine 1o, 2-furylimine 1p, and 2thienylimine 1q (Table 2, entries [10][11][12].…”

“…performed using TMSN 3 and Bu 2 Sn(OAc) 2 to afford 18 in a high yield. 11 The assumed reaction cycle for the reaction of 1a and 2c using 3e was shown in Fig. 2.…”

Alkylation of 5-Substituted 1H-Tetrazoles via the Diazotization of Aliphatic Amines

“…Only a few monosubstituted tetrazoles (1 H -Tz) are commercially available, and substrates were typically prepared via a 1,3-dipolar cycloaddition between a nitrile and sodium azide using Bronsted or Lewis acid catalysts or an organometallic azide reagent . Among these methods, reaction conditions using trimethylsilyl azide and a catalytic amount of tin oxide were found to be highly efficient to synthesize a large variety of tetrazoles. − To streamline the synthesis of 2,5-Tz, we devised a multicomponent one-pot process that combines the cycloaddition and the alkylation step from the corresponding nitrile. Not only the efficiency of the process would be improved, but such a one-pot procedure would also allow the use of 1 H -Tz unsuitable for isolation.…”