6291-28-7Relevant academic research and scientific papers
Chemoselective Synthesis of α-Amino-α-cyanophosphonates by Reductive Gem-Cyanation-Phosphonylation of Secondary Amides
Chen, Ting-Ting,Wang, Ai-E,Huang, Pei-Qiang
supporting information, p. 3808 - 3812 (2019/05/24)
A novel approach to α-amino-α-cyanophosphonates has been developed. The method features a Tf2O-mediated reductive geminal cyanation/phosphonylation of secondary amides. Mild reaction conditions, high bond-forming efficiency, inexpensive readily available starting materials, and good to excellent yields with wide functional group compatibility constitute the main advantages of this method. The protocol can be run on a gram scale.
Tf2O-Mediated Intermolecular Coupling of Secondary Amides with Enamines or Ketones: A Versatile and Direct Access to β-Enaminones
Liu, Yong-Peng,Zhu, Cheng-Jie,Yu, Cun-Cun,Wang, Ai-E,Huang, Pei-Qiang
supporting information, p. 7169 - 7174 (2019/11/16)
Based on the Tf2O-mediated intermolecular reaction of secondary amides with enamines derived from ketones, a novel approach to β-enaminones has been developed. The reaction is widely functional group tolerant and highly chemoselective. In the presence of 4 ? molecular sieves, the method can be extended to the one-pot condensation of secondary amides with ketones for NH β-enaminones synthesis.
Metal–Organic Framework Based on Copper and Carboxylate-Imidazole as Robust and Effective Catalyst in the Oxidative Amidation of Carboxylic Acids and Formamides
Albert-Soriano, María,Pastor, Isidro M.
supporting information, p. 5180 - 5188 (2016/10/26)
A metal–organic framework (MOF) based on copper and 1,3-bis(carboxymethyl)imidazole (bcmim) was prepared on a gram scale by using a precipitation method at room temperature. The Cu(bcmim)2MOF was shown to be an efficient catalyst for the preparation of amides through an oxidative coupling between carboxylic acids and formamides in the presence of an oxidant, such as tert-butyl hydroperoxide (TBHP). The method for the preparation of the amides is robust regardless of the carboxylic acid and gives good conversions with good selectivity. The heterogeneous catalyst was recovered unaltered after the reaction, was easily separated from the reaction mixture, and subsequently reactivated by suitable treatment. Moreover, the coupling reaction was scaled up to a gram scale, which allowed for the preparation of valuable products, such as fatty acid amides (i.e., 1-palmitoylpiperidine).
Solvent-free aromatic C-H functionalisation/halogenation reactions
Bedford, Robin B.,Engelhart, Jens U.,Haddow, Mairi F.,Mitchell, Charlotte J.,Webster, Ruth L.
supporting information; experimental part, p. 10464 - 10472 (2011/01/05)
The solvent-free, palladium-catalysed reaction of anilides with CuCl 2 in the presence or absence of copper acetate yields ortho-chlorinated anilides in good to excellent yields, even on a large scale (100 mmol). By contrast, the equivalent reactions with copper bromide, either solvent free or in 1,2-dichloroethane, in the presence or absence of palladium, under air or inert conditions, gave the products of simple electrophilic bromination. Mechanistic studies highlighted the involvement of palladacyclic intermediates, one of which was characterised crystallographically, which undergo subsequent reaction with copper(ii) chloride to yield the chlorinated anilide products.
The halogenation of some benzamides takes place preferentially at the ortho,para positions
Dong, Chang-Zhi,Julia, Marc,Tang, Jie
, p. 1689 - 1696 (2007/10/03)
The orientation of chlorination and bromination of N,N-disubstituted benzamides in aqueous acetic acid is strongly influenced by the nature of the alkyl groups at the nitrogen atom. With large groups, the halogenation takes place fairly selectively at the ortho/para positions.
