Iron/O2-Promoted C-H Bond Functionalization for the Exclusive Synthesis of 2-Quinoline Carboxaldehydes under Microwave Irradiation

doi:10.6023/cjoc201903007

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3294-3298.DOI: 10.6023/cjoc201903007 Previous Articles Next Articles

Special Issue: 碳氢活化合辑2018-2019

微波辅助下通过Fe/O₂催化C-H键官能团化合成喹啉-2-甲醛类化合物

谢庭辉^a^b, 蒋筱莹^a, 米治胜^a, 李雪^a, 徐小河^a, 白仁仁^a, 帅棋^a, 谢媛媛^a*()

^a 浙江工业大学药学院长三角绿色制药协同创新中心杭州 310014
^b 台州科技职业学院浙江台州 318020

收稿日期:2019-03-04 发布日期:2019-07-09
通讯作者: 谢媛媛 E-mail:xyycz@zjut.edu.cn
基金资助:
国家自然科学基金(21576239)

Iron/O₂-Promoted C-H Bond Functionalization for the Exclusive Synthesis of 2-Quinoline Carboxaldehydes under Microwave Irradiation

Xie Tinghui^a^b, Jiang Xiaoying^a, Mi Zhisheng^a, Li Xue^a, Xu Xiaohe^a, Bai Renren^a, Shuai Qi^a, Xie Yuanyuan^a*()

^a Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceutical, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014
^b College of Agriculture and Bioengineering, Taizhou Vocational College of Science and Technology, Taizhou, Zhejiang 318020

Received:2019-03-04 Published:2019-07-09
Contact: Xie Yuanyuan E-mail:xyycz@zjut.edu.cn
Supported by:
the National Natural Science Foundation of China(21576239)

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Abstract

An one-pot iron-catalyzed oxidative formylation of 2-methylquinolines to produce 2-quinoline carboxaldehydes under microwave irradiation has been achieved by employing O₂ as the oxygen donor. The reaction was general for the substrates with a wide range of functional groups, providing a yield of 48%~80%. The preliminary mechanistic studies revealed that the reaction underwent a radical pathway. Advantages of this method include the easy operation, short reaction time and good selectivity.

Key words: 2-quinoline carboxaldehydes, iron catalysis, C-H oxidation, microwave irradiation

Cite this article

Xie Tinghui, Jiang Xiaoying, Mi Zhisheng, Li Xue, Xu Xiaohe, Bai Renren, Shuai Qi, Xie Yuanyuan. Iron/O₂-Promoted C-H Bond Functionalization for the Exclusive Synthesis of 2-Quinoline Carboxaldehydes under Microwave Irradiation[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3294-3298.

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Fig. & Tab. 6

References 22

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Entry	Promoter	Fe³⁺/1a (molar ratio)	Solvent	Temp./℃	Time^b/min	Yield^c/%
1	FeCl₂	1/1	DMSO	130	30	Trace
2	FeCl₃	1/1	DMSO	130	10	60
3	FeCl₃·6H₂O	1/1	DMSO	130	10	62
4	Fe(NO₃)₃·9H₂O	1/1	DMSO	130	10	65
5	Fe(NO₃)₃·9H₂O	0.5/1	DMSO	130	10	46
6	Fe(NO₃)₃·9H₂O	1.5/1	DMSO	130	10	58
7	Fe(NO₃)₃·9H₂O	1/1	DMF	130	15	61
8	Fe(NO₃)₃·9H₂O	1/1	Toluene	130	30	53
9	Fe(NO₃)₃·9H₂O	1/1	Dioxane	130	30	48
10	Fe(NO₃)₃·9H₂O	1/1	DMAC	130	15	60
11	Fe(NO₃)₃·9H₂O	1/1	DMSO	140	8	70
12	Fe(NO₃)₃·9H₂O	1/1	DMSO	150	5	78
13	Fe(NO₃)₃·9H₂O	1/1	DMSO	160	5	71
14	Fe(NO₃)₃·9H₂O	1/1	DMSO	150	1	37
15	Fe(NO₃)₃·9H₂O	1/1	DMSO	150	10	76
16^d	Fe(NO₃)₃·9H₂O	1/1	DMSO	150	30	45
17^e	Fe(NO₃)₃·9H₂O	1/1	DMSO	150	30	18


Entry	Promoter	Fe³⁺/1a (molar ratio)	Solvent	Temp./℃	Time^b/min	Yield^c/%
1	FeCl₂	1/1	DMSO	130	30	Trace
2	FeCl₃	1/1	DMSO	130	10	60
3	FeCl₃·6H₂O	1/1	DMSO	130	10	62
4	Fe(NO₃)₃·9H₂O	1/1	DMSO	130	10	65
5	Fe(NO₃)₃·9H₂O	0.5/1	DMSO	130	10	46
6	Fe(NO₃)₃·9H₂O	1.5/1	DMSO	130	10	58
7	Fe(NO₃)₃·9H₂O	1/1	DMF	130	15	61
8	Fe(NO₃)₃·9H₂O	1/1	Toluene	130	30	53
9	Fe(NO₃)₃·9H₂O	1/1	Dioxane	130	30	48
10	Fe(NO₃)₃·9H₂O	1/1	DMAC	130	15	60
11	Fe(NO₃)₃·9H₂O	1/1	DMSO	140	8	70
12	Fe(NO₃)₃·9H₂O	1/1	DMSO	150	5	78
13	Fe(NO₃)₃·9H₂O	1/1	DMSO	160	5	71
14	Fe(NO₃)₃·9H₂O	1/1	DMSO	150	1	37
15	Fe(NO₃)₃·9H₂O	1/1	DMSO	150	10	76
16^d	Fe(NO₃)₃·9H₂O	1/1	DMSO	150	30	45
17^e	Fe(NO₃)₃·9H₂O	1/1	DMSO	150	30	18


Entry	X	R	Time^b/min	Fe³⁺/1 (molar ratio)	Product	Yield^c/%
1	CH	H	5	1.0	2a	78
2	CH	6-OMe	10	1.5	2b	60
3	CH	7-OMe	10	1.5	2c	64
4	CH	3-Me	10	1.5	2d	54
5	CH	6-Me	10	1.5	2e	63
6	CH	8-Me	10	1.5	2f	48
7	CH	8-Cl	5	1.0	2g	52
8	CH	6-NO₂	5	1.0	2h	81
9	CH	6-F	5	1.0	2i	73
10	CH	6-Cl	5	1.0	2j	67
11	N	H	5	1.0	2k	80


Entry	X	R	Time^b/min	Fe³⁺/1 (molar ratio)	Product	Yield^c/%
1	CH	H	5	1.0	2a	78
2	CH	6-OMe	10	1.5	2b	60
3	CH	7-OMe	10	1.5	2c	64
4	CH	3-Me	10	1.5	2d	54
5	CH	6-Me	10	1.5	2e	63
6	CH	8-Me	10	1.5	2f	48
7	CH	8-Cl	5	1.0	2g	52
8	CH	6-NO₂	5	1.0	2h	81
9	CH	6-F	5	1.0	2i	73
10	CH	6-Cl	5	1.0	2j	67
11	N	H	5	1.0	2k	80

微波辅助下通过Fe/O₂催化C-H键官能团化合成喹啉-2-甲醛类化合物

Iron/O₂-Promoted C-H Bond Functionalization for the Exclusive Synthesis of 2-Quinoline Carboxaldehydes under Microwave Irradiation

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微波辅助下通过Fe/O2催化C-H键官能团化合成喹啉-2-甲醛类化合物