Deoxyamination of N1-Triflylbenzotriazoles with Alcohols for sp3-C—N Bond Formation

doi:10.6023/cjoc202602011

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (5): 2017-2030.DOI: 10.6023/cjoc202602011 Previous Articles Next Articles

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N1-三氟甲磺酰苯并三唑与醇的脱氧胺化反应: sp³-C—N键的构建

胡泽宇^a^,^†, 邓家诚^a^,^†, 李延^a^,^†, 沈磊^b, 毛辉^b^,^*(), 周列锦^a^,^*()

^a 浙江师范大学化学与材料科学学院浙江金华 321004
^b 金华职业技术大学制药工程学院浙江金华 321017
^c 杭州下沙生物科技有限公司杭州 310000

收稿日期:2026-02-10 修回日期:2026-02-22 发布日期:2026-03-06
作者简介:
†共同第一作者
基金资助:
国家自然科学基金(22471241)

Deoxyamination of N1-Triflylbenzotriazoles with Alcohols for sp³-C—N Bond Formation

Zeyu Hu^a, Jiacheng Deng^a, Yan Li^a, Lei Shen^b, Hui Mao^b^,^*(), Liejin Zhou^a^,^*()

^a College of Chemistry and Materials Science, Zhejiang Normal University, Jinhua, Zhejiang 321004
^b College of Pharmaceutical Engineering, Jinhua University of Vocational Technology, Jinhua, Zhejiang 321017
^c Hangzhou Xiasha Biotechnology Co., Ltd., Hangzhou 310000

Received:2026-02-10 Revised:2026-02-22 Published:2026-03-06
Contact: * E-mail: ljzhou@zjnu.cn; maohui1988@126.com
About author:
These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22471241)

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Abstract

The construction of sp³-C—N bond remains a pivotal objective in organic chemistry, driven by the widespread presence of amine motifs in pharmaceuticals, materials, and agrochemicals. Herein, we report a practical and efficient method for sp³-C—N bond formation between N1-triflylbenzotriazoles and readily accessible alcohols. This transformation proceeds under mild conditions and exhibits a broad substrate scope. Moreover, other heterocycles, including pyrazoles and indazoles, are also compatible with this protocol.

Key words: benzotriazole, deoxyamination, alcohol, sp³-C—N bond

Cite this article

Zeyu Hu, Jiacheng Deng, Yan Li, Lei Shen, Hui Mao, Liejin Zhou. Deoxyamination of N1-Triflylbenzotriazoles with Alcohols for sp³-C—N Bond Formation[J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 2017-2030.

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References 17

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Entry ^a	Base	Solvent	Yield^b/%
1	Cs₂CO₃	DCE	68
2	Cs₂CO₃	THF	67
3	Cs₂CO₃	PhCl	62
4	Cs₂CO₃	Acetone	17
5	Cs₂CO₃	MeCN	44
6	Cs₂CO₃	1,4-Dioxane	77
7	NaOMe	1,4-Dioxane	nd^c
8	K₂CO₃	1,4-Dioxane	40
9	NaOH	1,4-Dioxane	13
10	t-BuOK	1,4-Dioxane	34
11	DBU	1,4-Dioxane	19
12^d	Cs₂CO₃	1,4-Dioxane	70
13^e	Cs₂CO₃	1,4-Dioxane	92
14^f	Cs₂CO₃	1,4-Dioxane	99^g

Entry ^a	Base	Solvent	Yield^b/%
1	Cs₂CO₃	DCE	68
2	Cs₂CO₃	THF	67
3	Cs₂CO₃	PhCl	62
4	Cs₂CO₃	Acetone	17
5	Cs₂CO₃	MeCN	44
6	Cs₂CO₃	1,4-Dioxane	77
7	NaOMe	1,4-Dioxane	nd^c
8	K₂CO₃	1,4-Dioxane	40
9	NaOH	1,4-Dioxane	13
10	t-BuOK	1,4-Dioxane	34
11	DBU	1,4-Dioxane	19
12^d	Cs₂CO₃	1,4-Dioxane	70
13^e	Cs₂CO₃	1,4-Dioxane	92
14^f	Cs₂CO₃	1,4-Dioxane	99^g

N1-三氟甲磺酰苯并三唑与醇的脱氧胺化反应: sp³-C—N键的构建

Deoxyamination of N1-Triflylbenzotriazoles with Alcohols for sp³-C—N Bond Formation

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N1-三氟甲磺酰苯并三唑与醇的脱氧胺化反应: sp3-C—N键的构建