2-chloro-5,6,7,8-tetrahydroquinolin-8-ol

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CAS: 130861-73-3
MF: C9H10NOCl
MW: 183.6348
Synonyms: 2-chloro-5,6,7,8-tetrahydroquinolin-8-ol

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Nan Sun

Zhejiang University of Technology
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Zhenlu Shen

Zhejiang University of Technology
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Co-reporter: Zhenlu Shen, Lili Sheng, Xiaochu Zhang, Weimin Mo, Baoxiang Hu, Nan Sun, Xinquan Hu
pp: 1579-1583
Publication Date(Web):20 March 2013
DOI: 10.1016/j.tetlet.2013.01.045
A facile and efficient protocol for the oxidative deprotection of benzyl-type ethers has been developed. The reaction was performed with catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert-butyl nitrite (TBN) under atmospheric pressure of O2. Under the optimal reaction conditions, a variety of p-methoxybenzyl (PMB), p-phenylbenzyl (PPB), and benzyl (Bn) ethers can be deprotected to their corresponding alcohols in excellent conversions and selectivities.A facile and efficient protocol for the oxidative deprotection of benzyl-type ethers has been developed. The reaction was performed with catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert-butyl nitrite (TBN) under atmospheric pressure of O2. Under the optimal reaction conditions, a variety of PMB, PPB, and Bn ethers can be deprotected to their corresponding alcohols in excellent conversions and selectivities.Image for unlabelled figure
Co-reporter: Zhenlu Shen, Meng Chen, Tiantian Fang, Meichao Li, Weimin Mo, Baoxiang Hu, Nan Sun, Xinquan Hu
pp: 2768-2772
Publication Date(Web):20 May 2015
DOI: 10.1016/j.tetlet.2015.04.033
A facile and efficient protocol for direct transformation of p-methoxybenzyl (PMB) ethers to aldehydes or ketones via a catalytic aerobic oxidation process has been developed. The reaction was performed with the combination of catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), 2,2,6,6-tetramethylpiperidine N-oxy (TEMPO), and tert-butyl nitrite (TBN), with molecular oxygen as terminal oxidant. A variety of PMB ether substrates derived from benzylic alcohols, heteroaromatic alcohols, and aliphatic alcohols, were converted to their corresponding carbonyl compounds in good conversions and selectivities.A facile and efficient protocol for direct transformation of p-methoxybenzyl (PMB) ethers to aldehydes or ketones via a catalytic aerobic oxidation process has been developed. The reaction was performed with the combination of catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), 2,2,6,6-tetramethylpiperidine N-oxy (TEMPO), and tert-butyl nitrite (TBN), with molecular oxygen as terminal oxidant. A variety of PMB ether substrates derived from benzylic alcohols, heteroaromatic alcohols, and aliphatic alcohols, were converted to their corresponding carbonyl compounds in good conversions and selectivities.Image for unlabelled figure

Weimin Mo

Zhejiang University of Technology
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Xinquan Hu

Zhejiang University of Technology
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Co-reporter: Zhenlu Shen, Lili Sheng, Xiaochu Zhang, Weimin Mo, Baoxiang Hu, Nan Sun, Xinquan Hu
pp: 1579-1583
Publication Date(Web):20 March 2013
DOI: 10.1016/j.tetlet.2013.01.045
A facile and efficient protocol for the oxidative deprotection of benzyl-type ethers has been developed. The reaction was performed with catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert-butyl nitrite (TBN) under atmospheric pressure of O2. Under the optimal reaction conditions, a variety of p-methoxybenzyl (PMB), p-phenylbenzyl (PPB), and benzyl (Bn) ethers can be deprotected to their corresponding alcohols in excellent conversions and selectivities.A facile and efficient protocol for the oxidative deprotection of benzyl-type ethers has been developed. The reaction was performed with catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert-butyl nitrite (TBN) under atmospheric pressure of O2. Under the optimal reaction conditions, a variety of PMB, PPB, and Bn ethers can be deprotected to their corresponding alcohols in excellent conversions and selectivities.Image for unlabelled figure
Co-reporter: Zhenlu Shen, Meng Chen, Tiantian Fang, Meichao Li, Weimin Mo, Baoxiang Hu, Nan Sun, Xinquan Hu
pp: 2768-2772
Publication Date(Web):20 May 2015
DOI: 10.1016/j.tetlet.2015.04.033
A facile and efficient protocol for direct transformation of p-methoxybenzyl (PMB) ethers to aldehydes or ketones via a catalytic aerobic oxidation process has been developed. The reaction was performed with the combination of catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), 2,2,6,6-tetramethylpiperidine N-oxy (TEMPO), and tert-butyl nitrite (TBN), with molecular oxygen as terminal oxidant. A variety of PMB ether substrates derived from benzylic alcohols, heteroaromatic alcohols, and aliphatic alcohols, were converted to their corresponding carbonyl compounds in good conversions and selectivities.A facile and efficient protocol for direct transformation of p-methoxybenzyl (PMB) ethers to aldehydes or ketones via a catalytic aerobic oxidation process has been developed. The reaction was performed with the combination of catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), 2,2,6,6-tetramethylpiperidine N-oxy (TEMPO), and tert-butyl nitrite (TBN), with molecular oxygen as terminal oxidant. A variety of PMB ether substrates derived from benzylic alcohols, heteroaromatic alcohols, and aliphatic alcohols, were converted to their corresponding carbonyl compounds in good conversions and selectivities.Image for unlabelled figure

WenJuan Zhang

Institute of Chemistry
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MeiChao Li

Zhejiang University of Technology
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