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• 100-61-8 N-methylaniline 
• 614-00-6 N-methyl-N-nitrosoaniline 

Relevant academic research and scientific papers

Phosphine-free hydrazone-Pd complex as the catalyst precursor for a Suzuki-Miyaura reaction under mild aerobic conditions

(Chemical Equation Presented) Glyoxal bis(N-methyl-N-phenylhydrazone) (1) and its related compounds such as 2-pyridinecarboxaldehyde N-methyl-N- phenylhydrazone (3) were prepared and examined as ligands for the Suzuki-Miyaura cross-coupling reaction of aryl halides and arylboronic acids. We found phosphine-free catalysts, such as Pd(OAc)2/hydrazone ligand 1 or 3, to be efficient catalysts for a variety of substrates to produce the coupling products in good yields.

Rh(iii)-catalyzed, hydrazine-directed C-H functionalization with 1-alkynylcyclobutanols: A new strategy for 1: H -indazoles

Rh(iii)-catalyzed coupling of phenylhydrazines with 1-alkynylcyclobutanols was realized through a hydrazine-directed C-H functionalization pathway. This [4+1] annulation, based on the cleavage of a Csp-Csp triple bond in alkynylcyclobutanol, provides a new pathway to prepare diverse 1H-indazoles under mild reaction conditions. This journal is

Higher Order Constitutional Dynamic Networks: [2×3] and [3×3] Networks Displaying Multiple, Synergistic and Competitive Hierarchical Adaptation

The present study investigates the constitutional dynamic networks (CDNs) underlying dynamic covalent libraries (DCLs) that extend beyond the [2×2] case toward higher orders, namely [2×3] and [3×3] CDNs involving respectively six and nine constituents generated from the recombination of five and six components linked through reversible chemical reactions. It explores the behavior of such systems under the action of one or two effectors. More specifically and for the sake of proof of principle, it makes use of DCLs involving dynamic organic ligands and analyzes their single and double adaptive response under the action of one and two metal cation effectors. Thus, interconversions within [2×3] DCLs of six constituents (hydrazone, acylhydrazone, and imine ligands) give access to the generation of [2×3] CDNs of 3D trigonal prismatic type consisting of three [2×2] sub-networks and presenting specific responses to the application of Cu+ and Zn2+ metal cation effectors, in particular double agonistic amplification. More complex [3×3] CDNs based on nine ligand constituents of imine, hydrazone, and acylhydrazone types were also designed and subjected to the application of one or two effectors, e.g., Cu+ and Fe2+ metal cations, revealing novel types of adaptive behavior: (i) agonistic amplification between a single constituent and a full [2×2] sub-network, and (ii) agonistic amplification along a single diagonal connecting three constituents. Of special interest is also the dependence of the response of the system to hierarchical sequence of effector application, whereby initial interaction with Cu+ ions results in the destruction of the network, whereas the sequence Fe2+ followed by Cu+ yields a clean three-constituent DCL. Finally and strikingly, the present results also demonstrate that the increase in complexity of the system by introduction of an additional entity leads to a simpler output through dynamic competition between components.

Transition-Metal-Free Trifluoromethylation of Aldehyde Derivatives with Sodium Trifluoromethanesulfinate

A metal-free and cost-effective synthetic protocol for the trifluoromethylation of N,N-disubstituted hydrazones with Langlois's reagent (CF3SO2Na) to afford the corresponding functionalized trifluoromethyl ketone hydrazones has been established. It is proposed that a radical/SET mechanism proceeding via a trifluoroalkyl radical may be involved in the reaction. Applications of the methodology in industry will be found and the development of new methods for trifluoromethylation with Langlois's reagent will be continued in our laboratory.

Adaptation in constitutional dynamic libraries and networks, switching between orthogonal metalloselection and photoselection processes

Constitutional dynamic libraries of hydrazones aAbB and acylhydrazones aAcC undergo reorganization and adaptation in response to a chemical effector (metal cations) or a physical stimulus (light). The set of hydrazones [1A1B, 1A2B, 2A1B, 2A 2B] undergoes metalloselection on addition of zinc cations which drive the amplification of Zn(1A2B)2 by selection of the fittest component 1A2B. The set of acylhydrazones [E-1A1C, 1A2C, 2A1C, 2A2C] undergoes photoselection by irradiation of the system, which causes photoisomerization of E- 1A1C into Z-1A1C with amplification of the latter. The set of acyl hydrazones [E-1A1C, 1A3C, 2A1C, 2A 3C] undergoes a dual adaptation via component exchange and selection in response to two orthogonal external agents: a chemical effector, metal cations, and a physical stimulus, light irradiation. Metalloselection takes place on addition of zinc cations which drive the amplification of Zn( 1A3C)2 by selection of the fittest constituent 1A3C. Photoselection is obtained on irradiation of the acylhydrazones that leads to photoisomerization from E-1A 1C to Z-1A1C configuration with amplification of the latter. These changes may be represented by square constitutional dynamic networks that display up-regulation of the pairs of agonists ( 1A2B, 2A1B), (Z-1A 1C, 2A2C), (1A3C, 2A1C), (Z-1A1C, 2A 3C) and the simultaneous down-regulation of the pairs of antagonists (1A1B, 2A2B), (1A 2C, 2A1C), (E-1A1C, 2A3C), (1A3C, 2A 1C). The orthogonal dual adaptation undergone by the set of acylhydrazones amounts to a network switching process.

Catalytic acceptorless dehydrogenative coupling of arylhydrazines and alcohols for the synthesis of arylhydrazones

The direct synthesis of arylhydrazones via catalytic acceptorless dehydrogenative coupling of arylhydrazines and alcohols has been accomplished. More importantly, complete selectivity for arylhydrazones and none of the N-alkylated byproducts were generated in this process, which exhibit new potential and provide a new horizon for the development of catalytic acceptorless dehydrogenative coupling reactions.