N,N,N',N'-四甲基-对苯二胺的胺官能化，用于在绿色条件下电合成各种对苯二胺,New Journal of Chemistry

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N,N,N',N'-四甲基-对苯二胺的胺官能化，用于在绿色条件下电合成各种对苯二胺
New Journal of Chemistry ( IF 2.7 ) Pub Date : 2021-08-10 , DOI: 10.1039/d1nj02737a
Fahimeh Varmaghani _{1,

2} , Maryam Abbasi ₁

Affiliation

TMPD ²⁺ /TMPD, N , N , N ', N '-四甲基-对苯二胺(TMPD)的伏安图特征反映了TMPD ²⁺在水溶液中的强烈不稳定性。TMPD ²⁺的不稳定性极大地限制了其在电化学合成中的应用。本文的显着特点是通过胺官能化稳定这种氧化还原活性物质。该过程从 TMPD 与亚硝酸钠的化学反应开始，生成N- (2-nitro-4-(二甲氨基)苯基) -N-甲基硝胺 (NDPM)。NDPM 的硝基官能团被电化学还原为相应的胺衍生物N- (2-氨基-4-(二甲氨基)苯基) -N-甲基硝酰胺 (ADPM)。与 TMPD ²⁺ /TMPD不同，ADPM的伏安结果在低氧化还原电位下呈现可逆的氧化还原过程。这种现象将 ADPM 作为一种有效的化合物，用于在绿色条件下电化学合成对苯二胺衍生物。为了检验这个假设，我们开发了一种配对电化学合成方法，通过在作为典型亲核试剂的芳基亚磺酸存在下，在阴极表面还原 NDPM，然后在阳极表面氧化。在没有氧化还原介质的绿色条件下成功地进行了电化学合成。

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Amine functionalization of N,N,N′,N′-tetramethyl-p-phenylenediamine for the electrosynthesis of a wide range of p-phenylenediamines in green conditions

The voltammogram features of TMPD²⁺/TMPD, N,N,N′,N′-tetramethyl-p-phenylenediamine (TMPD), reflect the intensive instability of TMPD²⁺ in aqueous solutions. The instability of TMPD²⁺ strongly restricts its application in electrochemical syntheses. The striking feature of this paper is the stabilization of this redox-active species via amine functionalization. The procedure started with the chemical reaction of TMPD with sodium nitrite to produce N-(2-nitro-4-(dimethylamino)phenyl)-N-methylnitramide (NDPM). The nitro functional group of NDPM was reduced electrochemically to the corresponding amine derivative, N-(2-amino-4-(dimethylamino)phenyl)-N-methylnitramide (ADPM). Unlike TMPD²⁺/TMPD, the voltammetric results of ADPM presented a reversible redox process at low redox potentials. The phenomenon introduces ADPM as an effective compound for the electrochemical synthesis of p-phenylenediamine derivatives in green conditions. To examine the hypothesis, we have developed a paired electrochemical synthesis method via the reduction of NDPM at the surface of the cathode followed by oxidation at the anode surface in the presence of arylsulfinic acids as typical nucleophiles. The electrochemical synthesis was successfully performed under green conditions in the absence of redox mediators.

更新日期：2021-08-24

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