Synthesis of Supported Indazolyl-Pyridyl-Quinoline Iridium Catalyst and Its Application to N-Alkylation of 2-Aminobenzothiazoles

doi:10.6023/cjoc202108026

Abstract

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

Cite this article

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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Fig. & Tab. 16

Figure 1. Pharmaceutically important organic amine

Scheme 1. Synthesis of ligand L1

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

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

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

Table 1. Optimization of reaction conditions

Table 2. Substrate scope of the reaction

Scheme 2. Control experiments

Scheme 3. Synthesis of ligand 4

Figure 6. Hammett plot equation

Figure 7. Intermediate research for the synthesis of 4aa

Scheme 4. Capture of intermediates

Scheme 5. Reaction mechanism of the synthesis of 4aa

Scheme 6. Recycled experiments of IPQ-Ir@MoS2

Scheme 7. Control experiment of catalytic synthesis 4aa

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

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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