铋催化二芳基重氮甲烷的X—H键插入反应

doi:10.6023/cjoc202601038

有机化学 ›› 2026, Vol. 46 ›› Issue (6): 2409-2414.DOI: 10.6023/cjoc202601038 上一篇下一篇

研究论文

铋催化二芳基重氮甲烷的X—H键插入反应

吕俊熙^a^,^†, 刘悦悦^a^,^†, 刘迅绅^a^,^†, 司志姚^a, 李欣泽^a, 陈奕诺^a, 刘路^a^,^b^,^*()

^a 华东师范大学化学与分子工程学院上海分子治疗与新药创制工程技术研究中心上海 200241
^b 石河子大学化学化工学院硅化工新材料兵团重点实验室新疆石河子 832003

收稿日期:2026-01-23 修回日期:2026-03-06 发布日期:2026-04-13
通讯作者: 刘路
作者简介:
^† 共同第一作者.
基金资助:
国家自然科学基金(22171088); 国家自然科学基金(22371074)

Bismuth-Catalyzed X—H Insertion of Diaryl Diazomethanes

Junxi Lü^a, Yueyue Liu^a, Xunshen Liu^a, Zhiyao Si^a, Xinze Li^a, Yinuo Chen^a, Lu Liu^a^,^b^,^*()

^a Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241
^b Key Laboratory of Silicon Chemical New Materials, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003

Received:2026-01-23 Revised:2026-03-06 Published:2026-04-13
Contact: Lu Liu
About author:
^† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22171088); National Natural Science Foundation of China(22371074)

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摘要/Abstract

发展了一种铋催化二芳基重氮的X—H (X=O, N, S)键插入反应. 该反应适用于多种含有X—H键的化合物, 包括醇、酚、酸、硫醇、硫酚以及苯胺. 该方法具有操作简单, 条件温和, 底物范围宽等特点, 为过渡金属参与的反应提供了一种替代方案, 同时进一步拓宽了金属铋在卡宾化学中的应用.

关键词: 铋催化, 二芳基重氮, X—H插入, 卡宾化学

A bismuth-catalyzed X—H bond insertion reaction of diaryl diazomethanes is developed. This reaction is compatible with a broad range of heteroatom-containing compounds, including alcohols, phenols, carboxylic acids, thiols, thiophenols and anilines. This protocol features simple operation, mild conditions and wide range of substrates, which provides an alternative approach to traditional transition-metal-catalyzed reactions. In addition, this method is expected to further expand the application of bismuth in carbene chemistry.

Key words: Bismuth catalysis, diaryldiazoalkanes, X—H bond insertion, carbene chemistry

引用此文

吕俊熙, 刘悦悦, 刘迅绅, 司志姚, 李欣泽, 陈奕诺, 刘路. 铋催化二芳基重氮甲烷的X—H键插入反应[J]. 有机化学, 2026, 46(6): 2409-2414.

Junxi Lü, Yueyue Liu, Xunshen Liu, Zhiyao Si, Xinze Li, Yinuo Chen, Lu Liu. Bismuth-Catalyzed X—H Insertion of Diaryl Diazomethanes[J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2409-2414.

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Entry	Catalyst	Solvent	Temp.^b/℃	Yield^c/%
1	—	DCM	30	NR
2	B(C₆F₅)₃	DCM	30	20
3	Rh₂(OAc)₄	DCM	30	ND
4	Sc(OTf)₃	DCM	30	14
5	Cu(OTf)₂	DCM	30	6
6	Bi(OTf)₃	DCM	30	26
7	BiCl₃	DCM	30	0
8	Bi(OTf)₃	Toluene	30	61
9	Bi(OTf)₃	THF	30	0
10	Bi(OTf)₃	MeCN	30	0
11	Bi(OTf)₃	Cyclohexane	30	40
12	Bi(OTf)₃	n-Hexane	30	78 (75)
13	Bi(OTf)₃	n-Hexane	20	72
14	Bi(OTf)₃	n-Hexane	40	74
15^d	Bi(OTf)₃	n-Hexane	30	13

Entry	Catalyst	Solvent	Temp.^b/℃	Yield^c/%
1	—	DCM	30	NR
2	B(C₆F₅)₃	DCM	30	20
3	Rh₂(OAc)₄	DCM	30	ND
4	Sc(OTf)₃	DCM	30	14
5	Cu(OTf)₂	DCM	30	6
6	Bi(OTf)₃	DCM	30	26
7	BiCl₃	DCM	30	0
8	Bi(OTf)₃	Toluene	30	61
9	Bi(OTf)₃	THF	30	0
10	Bi(OTf)₃	MeCN	30	0
11	Bi(OTf)₃	Cyclohexane	30	40
12	Bi(OTf)₃	n-Hexane	30	78 (75)
13	Bi(OTf)₃	n-Hexane	20	72
14	Bi(OTf)₃	n-Hexane	40	74
15^d	Bi(OTf)₃	n-Hexane	30	13

铋催化二芳基重氮甲烷的X—H键插入反应

Bismuth-Catalyzed X—H Insertion of Diaryl Diazomethanes

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