Palladium-Catalyzed ortho-Selective C—H Chlorination of Arenes Using Anodic Oxidation

doi:10.6023/A19040135

Acta Chimica Sinica ›› 2019, Vol. 77 ›› Issue (9): 866-873.DOI: 10.6023/A19040135 Previous Articles Next Articles

Special Issue: 有机自由基化学

Communication

电氧化促进的钯催化的芳烃C(sp ²)—H键氯代反应

杨启亮^a^b, 王向阳^c, 翁信军^b, 杨祥^b, 徐学涛^c, 童晓峰^a, 方萍^b, 伍新燕^a^*(), 梅天胜^b^*()

^a华东理工大学化学与分子工程学院结构可控先进功能材料及其制备教育部重点实验室上海 200237
^b中国科学院上海有机化学研究所金属有机化学国家重点实验室分子合成科学卓越中心上海 200032
^c五邑大学生物科技与大健康学院江门 529020

投稿日期:2019-04-19 发布日期:2019-05-08
通讯作者: 伍新燕,梅天胜 E-mail:xinyanwu@ecust.edu.cn;mei7900@sioc.ac.cn
基金资助:
项目受国家自然科学基金(Nos. 21772222);项目受国家自然科学基金(21821002);广东省教育厅基金资助.(Nos. 2017KTSCX185);广东省教育厅基金资助.(2017KSYS010);广东省教育厅基金资助(2016KCXTD005)

Palladium-Catalyzed ortho-Selective C—H Chlorination of Arenes Using Anodic Oxidation

Yang, Qi-Liang^a^b, Wang, Xiang-Yang^c, Weng, Xin-Jun^b, Yang, Xiang^b, Xu, Xue-Tao^c, Tong, Xiaofeng^a, Fang, Ping^b, Wu, Xin-Yan^a^*(), Mei, Tian-Sheng^b^*()

^aSchool of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237
^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
^c School of Biotechnology and Health Science, Wuyi University, Jiangmen 529020

Received:2019-04-19 Published:2019-05-08
Contact: Wu, Xin-Yan,Mei, Tian-Sheng E-mail:xinyanwu@ecust.edu.cn;mei7900@sioc.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China(Nos. 21772222);Project supported by the National Natural Science Foundation of China(21821002);Project supported by the National Natural Science Foundation of China(Nos. 2017KTSCX185);Project supported by the National Natural Science Foundation of China(2017KSYS010);Project supported by the National Natural Science Foundation of China(2016KCXTD005)

1. Palladium-Catalyzed ortho-Selective C—H Chlorination of Arenes Using Anodic Oxidation.PDF(6456KB)

Abstract

Aryl halides are key building blocks in organic synthesis for the construction of valuable natural products, medicinal and agricultural chemicals via transition metal-catalyzed coupling or substitution reactions. Halogenation is one of the most fundamental and important reactions in organic synthesis. Electrochemical transition-metal-catalyzed C—H functionalization has emerged as a powerful tool for molecular synthesis with the prospect of avoiding the use of costly and toxic oxidants or reductants, thereby reducing the footprint of undesirable, toxic byproducts. The palladium-catalyzed electrochemical C—H chlorination of benzamide derivatives directed by PIP amine directing group under divided cells has been demonstrated, in which readily available inorganic halides salts serve as halogen sources. The reaction features a broad substrate scope, high functional group tolerance, and compatibility of thiophene substrates. This reaction could be conducted on a gram scale, which is important for future application. Additionally, the sequential bromination and chlorination of C(sp ²)—H bond constructs highly functionalized aromatic carboxylic acid derivatives. The typical procedure is as follows: The electrolysis was carried out in an H-type divided cell (anion-exchange membrane), with a RVC anode (10 mm×10 mm×12 mm) and a platinum cathode (10 mm×10 mm×0.2 mm). The anodic chamber was charged with Pd(OAc)₂ (5.6 mg, 0.025 mmol, 10 mol%) and benzamide derivative (0.25 mmol, 1.0 equiv.) and dissolved in DMF (10 mL). LiCl (847.8 mg, 20.0 mmol) was added in the cathodic chamber and dissolved in water (10 mL). Then the reaction mixture was electrolyzed under a constant current of 5 mA at 90 ℃ until the complete consumption of the starting material as monitored by TLC or ¹H NMR. After the reaction, EtOAc (50 mL) was added to dilute the mixture and then washed with water (20 mL×3) and then with brine (20 mL). The organic fraction was dried over Na₂SO₄ and concentrated. The resulting residue was purified by silica gel flash chromatography to give the chlorination product.

Key words: organic electrosynthesis, transition metal catalysis, C—H activation, anodic oxidation, chlorination

Cite this article

Yang, Qi-Liang, Wang, Xiang-Yang, Weng, Xin-Jun, Yang, Xiang, Xu, Xue-Tao, Tong, Xiaofeng, Fang, Ping, Wu, Xin-Yan, Mei, Tian-Sheng. Palladium-Catalyzed ortho-Selective C—H Chlorination of Arenes Using Anodic Oxidation[J]. Acta Chimica Sinica, 2019, 77(9): 866-873.

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Fig. & Tab. 9

Figure 1. Palladium-catalyzed electrochemical chlorination

Entry	Variation from standard conditions above	Yield^b/%
1	none	92 (85)^c
2	PdCl₂ instead of Pd(OAc)₂	89
3	Pd(OCOCF₃)₂ instead of Pd(OAc)₂	91
4	DMA instead of DMF (anode)	80
5	HMPA instead of DMF (anode)	63
6	DMSO instead of DMF (anode)	12
7	H₂O instead of DMF (anode)	34
8	HCl instead of LiCl	72
9	NaCl instead of LiCl	71
10	NH₄Cl instead of LiCl	65
11	80 ℃ instead of 90 ℃	90
12	100 ℃ instead of 90 ℃	92
13	2.5 mA instead of 5 mA (24 h)	88
14	10 mA instead of 5 mA (6 h)	67
15	no Pd(OAc)₂	nr
16	no electric current	nr

Table 1. Optimization of chlorination conditions a

Table 2. Substrate scopea

Table 3. Sequential double C—H activationa

Figure 2. Gram-Scale Experiment

Figure 3. Summary of key mechanistic findings

Figure 4. Preparation and reactivity of monomeric palladacycle

Figure 5. Cyclic voltammograms recorded on a Pt electrode (area=0.03 cm2): (a) MeCN containing 0.1 mol/L n-Bu4NPF6; (b) solution (a) after addition of 5 mmol/L LiCl; (c) solution (a) after addition of 2 mmol/L palladacycle 5; (d) solution (b) after addition of 2 mmol/L palladacycle 5

Figure 6. Proposed catalytic cycle

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电氧化促进的钯催化的芳烃C(sp ²)—H键氯代反应

Palladium-Catalyzed ortho-Selective C—H Chlorination of Arenes Using Anodic Oxidation

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电氧化促进的钯催化的芳烃C(sp 2)—H键氯代反应

Palladium-Catalyzed ortho-Selective C—H Chlorination of Arenes Using Anodic Oxidation

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电氧化促进的钯催化的芳烃C(sp ²)—H键氯代反应