A Mild and Efficient Method for Formation of C–N Bond from Benzyl Alcohols and Sulfonamide, Carboxamide, 4-Nitroanline and Azide Catalysed by SnCl₄

Abstract

A mild and efficient method for the formation of C-N bonds is reported with SnCl 4 as an inexpensive catalyst. With 10 mol% of SnCl 4 , the direct substitution reaction of secondary benzyl alcohols with a sulfonamide, a carboxamide, 4-nitroaniline and an azide proceeds well in good to excellent yields at room temperature.

A Direct Brønsted Acid‐Catalyzed Azidation of Benzhydrols and Carbohydrates

“…Based on the positive results obtained for the benzhydrols, the newly developed methodology was applied to the more challenging carbohydrate substrates. It should be noted that many of the previous methodologies for the preparation of glycosyl azides rely on Mitsunobu‐like conditions with metal azides and hydrazoic acid or by the reaction of unstable glycosyl halides with sodium azide . Remarkably, the conditions used for the benzhydrols led to a 67 % yield with an α/β ratio of 3.3:1 when applied to 2,3,5‐tri‐O‐benzyl‐ β ‐D‐arabinofuranose.…”

“…(Azidomethylene)dibenzene (1c): The title compound was prepared from diphenylmethanol using 0.4 eq. HBF 4 · OEt 2 following general procedure 2.2.…”

Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO2 as a catalyst through Box–Behnken experimental design

“…The [24] 6 5 8 5 6 9 -72 (68-71) [24] (Continues) produced pink crystals were filtered and washed with 5 ml of perchloric acid. [27] 10 4 8 5 9 7 -100 (98-99) [28] 11 5 82 Liquid (liquid) [29] 12 5.5 85 84-86 (82-84) [30] 13 6 8 0 9 2 -95 (93-95) [31] 14 5 84 119-121 (120-121) [32] (Continues) [27] 10 4 8 5 9 7 -100 (98-99) [28] 11 5 82 Liquid (liquid) [29] 12 5.5 85 84-86 (82-84) [30] 13 6 8 0 9 2 -95 (93-95) [31] 14 5 84 119-121 (120-121) [32] (Continues) …”