Direct Oxidative Conversion of Alcohols, Amines, Aldehydes, and Benzyl Halides into the Corresponding Nitriles with Trichloroisocyanuric Acid in Aqueous Ammonia

Abstract

A new and efficient procedure for the one-pot conversion of various alcohols, aldehydes and primary amines into the corresponding nitriles in excellent yields was easily achieved by trichloroisocyanuric acid (TCCA) as an oxidant and reagent in aqueous ammonia. Also, various benzylic halides were smoothly and directly converted into the corresponding aromatic nitriles in high yields under the same conditions.

Direct Synthesis of Nitriles from Aldehydes and Hydroxylamine Hydrochloride Catalyzed by a HAP@AEPH2-SO3H Nanocatalyst

“…Aromatic aldehydes bearing an electron-donating group afford the corresponding products rapidly in high yields (Table 4, entries 2-10). In contrast, the reaction of aromatic aldehydes with electron withdrawing substituents such as -Cl, -Br, -NO 2 , and -CN, require longer reaction times to proceed properly (Table 4, entries [11][12][13][14][15]. Moreover, it should be noted that the orthosubstituted aldehydes render lower yields (Table 4, entry 3, 8, 12) due to the steric hindrance.…”

“…[11] Other alternative methods for the synthesis of these compounds involve the one-step conversion of aldehydes into nitriles, which is one of the most efficient and cleanest routes for this transformation. [12] During the past decades, studies on the preparation of nitriles from aldehydes have received much attention and several methods are reported in the literature, which include using trichloroisocyanuric acid (TCCA), [13] dry alumina, [14] FeCl 3 , [15] graphite, [16] zinc oxide (ZnO), [17] Ag nanoparticles (NPs), [18] [BMIM(SO 3 …”

Efficient N-Boc protection of amines by a reusable heterogeneous solid acid nanocatalyst at room temperature

“…In continuation of our interest in use of solid acid catalysts in organic transformations [56][57][58][59][60][61][62][63] and our previous report on the synthesis and application of silica phenylsulfonic acid as a solid acid heterogeneous catalyst for one-pot synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles and bis(indolyl)methanes in water [56], we report herein the use of mesoporous silica phenylsulfonic acid (SBA-15-Ph-SO 3 H) as a recyclable and heterogeneous solid acid catalyst for N-tertbutoxycarbonylation of various structurally different amine derivatives (Scheme 1), the results of which are summarized in Table 1. In an initial study, aniline (1 mmol) was treated with (Boc) 2 O (1.1 mmol) and SBA-15-Ph-SO 3 H (0.004 g, 1 mol %) as a catalyst to isolate the corresponding mono N-Boc derivative within 2 min in 98 % yield.…”

Convenient One-Pot Synthesis of Sulfonamides from Thiols and Disulfides Using 1,3-Dichloro-5,5-dimethylhydantoin (DCH)

“…Herein, as part of our ongoing study on the application of N-halo reagents in organic synthesis, [13][14][15][16][17] we would like to present the direct convenient one-pot synthesis of sulfonamides from thiols and disulfides using 1,3-dichloro-5,5-dimethylhydantoin (DCH) under mild conditions (Scheme 1).…”