An Oxidative Strategy for Generating Trichloromethyl Radical from Carbon Tetrahalides: Transition-Metal-Free Synthesis of Trichloromethylated Oxindoles

doi:10.6023/cjoc202508011

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (3): 974-985.DOI: 10.6023/cjoc202508011 Previous Articles Next Articles

ARTICLES

一种由四卤化碳生成三氯甲基自由基的氧化策略: 无过渡金属合成三氯甲基化吲哚酮

周可^a^,^†, 王泽涌^a^,^†, 黎亚琳^b, 张倩^b, 李馨月^b, 邹汉芳^b, 张明忠^a^,^*(), 郭圣荣^a^,^*(), 陈铁桥^c

^a 丽水学院材料与能源工程学院浙江丽水 323000
^b 长江师范学院化学化工学院重庆 408000
^c 海南大学化学化工学院海口 570228

收稿日期:2025-08-08 修回日期:2025-11-27 发布日期:2025-12-25
通讯作者: 张明忠, 郭圣荣
作者简介:
†共同第一作者
基金资助:
丽水市科技计划(2023KJTP07); 丽水学院科研基金(QD2455); 丽水学院科研基金(ZXZK102024002)

An Oxidative Strategy for Generating Trichloromethyl Radical from Carbon Tetrahalides: Transition-Metal-Free Synthesis of Trichloromethylated Oxindoles

Ke Zhou^a, Zeyong Wang^a, Yalin Li^b, Qian Zhang^b, Xinyue Li^b, Hanfang Zou^b, Mingzhong Zhang^a^,^*(), Shengrong Guo^a^,^*(), Tieqiao Chen^c

^a College of Materials and Energy Engineering, Lishui University, Lishui, Zhejiang 323000
^b College of Chemistry and Chemical Engineering, Yangtze Normal University, Chongqing 408100
^c College of Chemistry and Chemical Engineering, Hainan University, Haikou 570228

Received:2025-08-08 Revised:2025-11-27 Published:2025-12-25
Contact: Mingzhong Zhang, Shengrong Guo
About author:
†These authors contributed equally to this work.
Supported by:
Science and Technology Plan of Lishui(2023KJTP07); Scientific Research Foundation of Lishui University(QD2455); Scientific Research Foundation of Lishui University(ZXZK102024002)

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Abstract

A novel oxidative protocol for the generation of trichloromethyl radical from the cleavage of C—X bond of carbon tetrahalides has been reported. This reaction employs the combination of potassium persulfate (K₂S₂O₈) and quaternary ammonium salt (QAS) as a radical triggered system, thereby enabling the transition-metal- and organic-peroxide-free synthesis of trichloromethylated oxindoles through cascade cyclization of alkenes. The protocol delivers both high to excellent yields and good functional group tolerance. Additionally, the combination can be applied to the synthesis of α-bromoketones from ketones via the oxidative cleavage of C(sp³)—H bonds.

Key words: radicals, cyclization, oxidation, transition-metal-free

Cite this article

Ke Zhou, Zeyong Wang, Yalin Li, Qian Zhang, Xinyue Li, Hanfang Zou, Mingzhong Zhang, Shengrong Guo, Tieqiao Chen. An Oxidative Strategy for Generating Trichloromethyl Radical from Carbon Tetrahalides: Transition-Metal-Free Synthesis of Trichloromethylated Oxindoles[J]. Chinese Journal of Organic Chemistry, 2026, 46(3): 974-985.

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Entry	Oxidant (equiv.)	QAS (equiv.)	Yield^b/%
1	K₂S₂O₈ (2.0)	TBAI (n-Bu₄NI, 2.0)	45
2	K₂S₂O₈ (2.0)	None	0
3	None	TBAI (n-Bu₄NI, 2.0)	0
4	K₂S₂O₈ (2.0)	TBAHS (n-Bu₄NHSO₄, 2.0)	47
5	K₂S₂O₈ (2.0)	TBAB (n-Bu₄NBr, 2.0)	10
6	K₂S₂O₈ (2.0)	BTBAB (n-Bu₃NBnBr, 2.0)	13
7	K₂S₂O₈ (2.0)	TBAF (n-Bu₄NF, 2.0)	65
8	K₂S₂O₈ (2.0)	TBAH (n-Bu₄NOH, 2.0)	73
9	K₂S₂O₈ (2.0)	TBAH (n-Bu₄NOH, 1.5)	80
10	K₂S₂O₈ (2.0)	TBAH (n-Bu₄NOH, 2.5)	85
11	K₂S₂O₈ (2.5)	TBAH (n-Bu₄NOH, 2.5)	92
12	K₂S₂O₈ (3.0)	TBAH (n-Bu₄NOH, 2.5)	95
13^c	K₂S₂O₈ (3.0)	TBAH (n-Bu₄NOH, 2.5)	83
14^d	K₂S₂O₈ (3.0)	TBAH (n-Bu₄NOH, 2.5)	91

Entry	Oxidant (equiv.)	QAS (equiv.)	Yield^b/%
1	K₂S₂O₈ (2.0)	TBAI (n-Bu₄NI, 2.0)	45
2	K₂S₂O₈ (2.0)	None	0
3	None	TBAI (n-Bu₄NI, 2.0)	0
4	K₂S₂O₈ (2.0)	TBAHS (n-Bu₄NHSO₄, 2.0)	47
5	K₂S₂O₈ (2.0)	TBAB (n-Bu₄NBr, 2.0)	10
6	K₂S₂O₈ (2.0)	BTBAB (n-Bu₃NBnBr, 2.0)	13
7	K₂S₂O₈ (2.0)	TBAF (n-Bu₄NF, 2.0)	65
8	K₂S₂O₈ (2.0)	TBAH (n-Bu₄NOH, 2.0)	73
9	K₂S₂O₈ (2.0)	TBAH (n-Bu₄NOH, 1.5)	80
10	K₂S₂O₈ (2.0)	TBAH (n-Bu₄NOH, 2.5)	85
11	K₂S₂O₈ (2.5)	TBAH (n-Bu₄NOH, 2.5)	92
12	K₂S₂O₈ (3.0)	TBAH (n-Bu₄NOH, 2.5)	95
13^c	K₂S₂O₈ (3.0)	TBAH (n-Bu₄NOH, 2.5)	83
14^d	K₂S₂O₈ (3.0)	TBAH (n-Bu₄NOH, 2.5)	91

Entry	Oxidant (equiv.)	Additive (equiv.)	Solvent	Yield^b/%
1	K₂S₂O₈ (2.0)	BTBAB (2.0)	PhCF₃	78
2^c	K₂S₂O₈ (2.0)	BTBAB (2.0)	PhCF₃	65
3	K₂S₂O₈ (2.0)	BTBAB (2.0)	DMF	0
4	K₂S₂O₈ (2.0)	BTBAB (2.0)	MeCN	Trace
5^d	K₂S₂O₈ (2.0)	BTBAB (2.0)	MeCN/H₂O	0
6	K₂S₂O₈ (2.0)	BTBAB (2.0)	MeNO₂	19
7	K₂S₂O₈ (2.0)	BTBAB (1.5)	PhCF₃	71
8	K₂S₂O₈ (2.0)	BTBAB (2.5)	PhCF₃	79
9	K₂S₂O₈ (2.5)	BTBAB (2.0)	PhCF₃	74
10	K₂S₂O₈ (2.0)	TBAB (2.0)	PhCF₃	39
11	K₂S₂O₈ (2.0)	KBr (2.0)	PhCF₃	Trace
12	(NH₄)₂S₂O₈ (2.0)	BTBAB (2.0)	PhCF₃	55
13	Na₂S₂O₈ (2.0)	BTBAB (2.0)	PhCF₃	23

Entry	Oxidant (equiv.)	Additive (equiv.)	Solvent	Yield^b/%
1	K₂S₂O₈ (2.0)	BTBAB (2.0)	PhCF₃	78
2^c	K₂S₂O₈ (2.0)	BTBAB (2.0)	PhCF₃	65
3	K₂S₂O₈ (2.0)	BTBAB (2.0)	DMF	0
4	K₂S₂O₈ (2.0)	BTBAB (2.0)	MeCN	Trace
5^d	K₂S₂O₈ (2.0)	BTBAB (2.0)	MeCN/H₂O	0
6	K₂S₂O₈ (2.0)	BTBAB (2.0)	MeNO₂	19
7	K₂S₂O₈ (2.0)	BTBAB (1.5)	PhCF₃	71
8	K₂S₂O₈ (2.0)	BTBAB (2.5)	PhCF₃	79
9	K₂S₂O₈ (2.5)	BTBAB (2.0)	PhCF₃	74
10	K₂S₂O₈ (2.0)	TBAB (2.0)	PhCF₃	39
11	K₂S₂O₈ (2.0)	KBr (2.0)	PhCF₃	Trace
12	(NH₄)₂S₂O₈ (2.0)	BTBAB (2.0)	PhCF₃	55
13	Na₂S₂O₈ (2.0)	BTBAB (2.0)	PhCF₃	23

一种由四卤化碳生成三氯甲基自由基的氧化策略: 无过渡金属合成三氯甲基化吲哚酮

An Oxidative Strategy for Generating Trichloromethyl Radical from Carbon Tetrahalides: Transition-Metal-Free Synthesis of Trichloromethylated Oxindoles

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