An efficient procedure for chemoselective amidation from carboxylic acid and amine (ammonium salt) under mild conditions

Li, Jianhui; He, Shaopo; Fu, Haiqing; Chen, Xin; Tang, Min; Zhang, Dela; Wang, Bo

doi:10.1007/s11164-017-3229-4

Cited by 8 publications

(7 citation statements)

References 55 publications

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“…Unless otherwise reported, DMT-Ams(ClO 4 ) were synthesized from CDMT with the corresponding tertiary amine and NaOCl 4 according to the synthetic procedure reported in the literature [ 43 , 53 ]. All products, 3a-3i , were characterized and purity was confirmed by comparison to the literature data [ 64 , 65 , 66 , 67 , 68 , 69 , 70 ].…”

Section: Methodsmentioning

confidence: 93%

Sustainable Triazine-Based Dehydro-Condensation Agents for Amide Synthesis

et al. 2021

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Conventional methods employed today for the synthesis of amides often lack of economic and environmental sustainability. Triazine-derived quaternary ammonium salts, e.g., 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM(Cl)), emerged as promising dehydro-condensation agents for amide synthesis, although suffering of limited stability and high costs. In the present work, a simple protocol for the synthesis of amides mediated by 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and a tert-amine has been described and data are compared to DMTMM(Cl) and other CDMT-derived quaternary ammonium salts (DMT-Ams(X), X: Cl− or ClO4−). Different tert-amines (Ams) were tested for the synthesis of various DMT-Ams(Cl), but only DMTMM(Cl) could be isolated and employed for dehydro-condensation reactions, while all CDMT/tert-amine systems tested were efficient as dehydro-condensation agents. Interestingly, in best reaction conditions, CDMT and 1,4-dimethylpiperazine gave N-phenethyl benzamide in 93% yield in 15 min, with up to half the amount of tert-amine consumption. The efficiency of CDMT/tert-amine was further compared to more stable triazine quaternary ammonium salts having a perchlorate counter anion (DMT-Ams(ClO4)). Overall CDMT/tert-amine systems appear to be a viable and more economical alternative to most dehydro-condensation agents employed today.

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Section: Methodsmentioning

confidence: 93%

Sustainable Triazine-Based Dehydro-Condensation Agents for Amide Synthesis

et al. 2021

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“…Multiphoton excitation catalysis has emerged as new strategy to overcome the thermodynamic limitations of visible light photoredox catalysis to generate high energy photoreductants. 14 Recently our group disclosed a method for the in-situ generation of a second highly reducing iridium photocatalyst from [Ir(ppy)2(dtbpy)] + via a 2-photon tandem photoredox cycle 15 ( Figure 2a) and Nicewicz uncovered similar behaviour with organophotoredox catalysts. 16 This strategy has been successfully applied to the reductive protodehalogenation of unactivated organohalides and showcases the ability common photoredox catalysts to yield a potent excited-state donors via multiphoton excitation.…”

Section: Introductionmentioning

confidence: 93%

“…Significantly, aryl bromides could be selectively carbonylated in the presence of boronates (10), demonstrating exquisite orthogonality to Pd-catalyzed carbonylative amidation where the Suzuki coupling typically dominates. 20 Deactivated substrates bearing electron donating substitution were well tolerated (12a-20) and steric sensitivity to ortho-methyl substituent was generally not observed (12)(13)(14). Under the developed reaction conditions, full conversion of the starting aryl halide was achieved for each example.…”

Section: Aminocarbonylation Of Aryl and Heteroaryl Halidesmentioning

confidence: 98%

Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides

Forni¹,

MICIC²,

Connell³

et al. 2020

Preprint

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We report a new visible light-mediated carbonylative amidation of aryl, heteroaryl and alkyl halides. A tandem catalytic cycle of [Ir(ppy)2(dtb-bpy)]+ generates a potent iridium photoreductant via a second catalytic cycle in the presence of DIPEA which productively engages aryl bromides, iodides and even chlorides as well as primary, secondary and tertiary alkyl iodides. The versatility of the in-situ generated catalyst is illustrated by compatibility with aliphatic and aromatic amines, high functional group tolerance and the late-stage amidation of complex natural products.

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“…The coupling products were obtained by one‐pot reaction of the phenols, DCID and phenylboronic acid in a single flask.DCID ( 2 ) is readily available from the reaction of dicyclohexylcarbodiimine (DCC) with oxalyl chloride by known reported methods . From a simple search in the literature, it can be seen that DCID has been used in very few reactions, for example Schilter et al reported the chlorodehydroxylation of alcohols using DCID, Guo and coworkers have recently reported Beckman's rearrangement of ketoximes and Wang et al have reported chemoselective amidation from carboxylic acid and amine using this compound …”

Section: Introductionmentioning

confidence: 99%

Dichloroimidazolidinedione‐activated one‐pot Suzuki–Miyaura cross‐coupling of phenols

Madankar

Mokhtari

Mirjafary

2020

Applied Organom Chemis

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The first general method for the Suzuki‐type cross‐coupling of phenols with aryl boronic acids using dichloroimidazolidinedione (DCID) as a new reagent is presented. In the presence of DCID and Pd/metal–organic framework (MOF), coupling of aryl boronic acids with a wide range of phenols, was carried out smoothly in tetrahydrofuran (THF) at reflux conditions to afford the cross‐coupling products in good to excellent yields. The structures of all compounds were corroborated by 1H‐ and 13C‐NMR. A plausible mechanism for this type of reaction is proposed.

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An efficient procedure for chemoselective amidation from carboxylic acid and amine (ammonium salt) under mild conditions

Cited by 8 publications

References 55 publications

Sustainable Triazine-Based Dehydro-Condensation Agents for Amide Synthesis

Sustainable Triazine-Based Dehydro-Condensation Agents for Amide Synthesis

Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides

Dichloroimidazolidinedione‐activated one‐pot Suzuki–Miyaura cross‐coupling of phenols

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