吲唑吡啶喹啉铱负载催化剂的合成及在2-氨基苯并噻唑N-烷基化反应中的应用

doi:10.6023/cjoc202108026

摘要/Abstract

设计合成了一种多氮唑类三齿配体, 并将其与铱配合物成功负载至MoS₂纳米片上, 制备出了非均相催化剂IPQ-Ir@MoS₂. 利用扫描电子显微镜(SEM)、透射电子显微镜(TEM)、X射线能谱仪(EDS)、X射线光电能谱(XPS), 对该催化剂进行表征与分析. 该催化剂能够实现2-氨基苯并噻唑与苯甲醇的无溶剂N-烷基化反应, 在反应中表现出优异的催化活性和良好的底物普适性, 对反应机理进行了探索.

关键词: 借氢, 脱氢, 三齿配体, 铱, 负载型催化剂

The tridentate indazolyl-pyridyl-quinoline ligand was designed and synthesized, and its iridium complex was successfully loaded on MoS₂ nanosheets. The resulting IPQ-Ir@MoS₂ was fully characterized by means of scanning electron microscope (SEM), transmission electron microscopy (TEM), energy dispersive spectrometer (EDS) and X-ray photoelectron spectrometry (XPS). This iridium composite could realize N-alkylation of 2-aminobenzothiazole with benzyl alcohol under solvent-free condition. It showed excellent catalytic activity and good tolerance. At the same time, the reaction mechanism was also explored.

Key words: borrowing hydrogen, dehydrogenation, tridentate ligand, iridium, supported catalyst

引用此文

李家豪, 刘洪强, 张博, 葛冰洋, 王大伟. 吲唑吡啶喹啉铱负载催化剂的合成及在2-氨基苯并噻唑N-烷基化反应中的应用[J]. 有机化学, 2022, 42(2): 619-630.

Jiahao Li, Hongqiang Liu, Bo Zhang, Bingyang Ge, Dawei Wang. Synthesis of Supported Indazolyl-Pyridyl-Quinoline Iridium Catalyst and Its Application to N-Alkylation of 2-Aminobenzothiazoles[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 619-630.

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图/表 16

图1. 医药上几种重要的有机胺

Figure 1. Pharmaceutically important organic amine

图式1. 配体L1的合成方法

Scheme 1. Synthesis of ligand L1

图2. (a, b) MoS2纳米片的SEM图; (c, d)非均相催化剂IPQ-Ir@MoS2的SEM图

Figure 2. (a, b) SEM images of MoS2; (c, d) SEM images of IPQ-Ir@MoS2

图3. (a, b) MoS2纳米片的TEM图; (c, d)非均相催化剂IPQ- Ir@MoS2的TEM图

Figure 3. (a, b) TEM images of MoS2; (c, d) TEM images of IPQ-Ir@MoS2

图4. IPQ-Ir@MoS2能谱元素衍射曲线

Figure 4. EDS spectra of IPQ-Ir@MoS2

Entry	Base	Time/h	Temp./℃	Yield/%
1	Na₂CO₃	16	130	<5
2	NaHCO₃	16	130	<5
3	K₂CO₃	16	130	45
4	Cs₂CO₃	16	130	85
5	KOtBu	16	130	82
6	NaOH	16	130	94
7^c	NaOH	16	130	94
8^d	NaOH	16	130	90
9	NaOH	12	130	90
10	NaOH	24	130	94
11	NaOH	16	110	78
12	NaOH	16	150	94
13	—	16	130	<5

表1. 反应条件优化a,b

Table 1. Optimization of reaction conditions

表2. 底物的普适性考察a,b

Table 2. Substrate scope of the reaction

图式2. 对照实验

Scheme 2. Control experiments

图式3. 配体4的合成

Scheme 3. Synthesis of ligand 4

图6. Hammett方程

Figure 6. Hammett plot equation

图7. 化合物4aa合成过程中中间体的研究.

Figure 7. Intermediate research for the synthesis of 4aa

图式4. 中间体捕获实验

Scheme 4. Capture of intermediates

图式5. 合成4aa的反应机理

Scheme 5. Reaction mechanism of the synthesis of 4aa

图式6. 催化剂IPQ-Ir@MoS2的回收试验

Scheme 6. Recycled experiments of IPQ-Ir@MoS2

图式7. 催化合成4aa对照实验

Scheme 7. Control experiment of catalytic synthesis 4aa

图式8. IPQ-Ir@MoS2催化合成N-苄基苯胺

Scheme 8. N-Benzyl aniline was synthesized by IPQ-Ir@MoS2

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