Visible Light-Promoted Aerobic Oxo-azidation of Alkenyl Silanes

doi:10.6023/cjoc202409002

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (5): 1684-1690.DOI: 10.6023/cjoc202409002 Previous Articles Next Articles

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可见光促进烯基硅化合物有氧氧化-叠氮化反应

谭燕^a, 应佳乐^b, 於兵^a^,^*(), 陆展^a^,^b^,^*()

^a 郑州大学化学学院郑州 450001
^b 浙江大学化学系杭州 310058

收稿日期:2024-11-01 修回日期:2024-11-21 发布日期:2024-12-05
基金资助:
国家重点研发计划(2021YFF0701600); 国家重点研发计划(2021YFA1500200); 国家自然科学基金(22271249); 中央高校基本科研业务费基金(226-2022-00224); 中央高校基本科研业务费基金(226-2024-00003); 浙江省自然科学基金(LDQ24B020001)

Visible Light-Promoted Aerobic Oxo-azidation of Alkenyl Silanes

Yan Tan^a, Jiale Ying^b, Bing Yu^a^,^*(), Zhan Lu^a^,^b^,^*()

^a College of Chemistry, Zhengzhou University, Zhengzhou 450001
^b Department of Chemistry, Zhejiang University, Hangzhou 310058

Received:2024-11-01 Revised:2024-11-21 Published:2024-12-05
Contact: * E-mail: luzhan@zju.edu.cn; bingyu@zzu.edu.cn
Supported by:
National Key R&D Program of China(2021YFF0701600); National Key R&D Program of China(2021YFA1500200); National Natural Science Foundation of China(22271249); Fundamental Research Funds for the Central Universities(226-2022-00224); Fundamental Research Funds for the Central Universities(226-2024-00003); Zhejiang Provincial Natural Science Foundation(LDQ24B020001)

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Abstract

A visible-light-enabled method for the synthesis of α-azidoketones has been developed via oxo-azidation of alkenyl silanes with trimethylsilylazide and molecular oxygen under mild conditions. The reaction could be carried out in gram scale. Various radical sources, including trifluoromethyl radical, thiocyanate radical, bromide radical, chlorine radical could participate effectively instead of azide radical in the reaction.

Key words: visible light catalysis, aerobic oxidation, alkenyl silanes, organic azides

Cite this article

Yan Tan, Jiale Ying, Bing Yu, Zhan Lu. Visible Light-Promoted Aerobic Oxo-azidation of Alkenyl Silanes[J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1684-1690.

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References 23

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Entry	Variation from the standard conditions	Yield^b/%
1	None	71 (63)
2	3CzClIPN as photocatalyst	53
3	Ir[dF(CF₃)ppy]₂(dtbpy)PF₆ as photocatalyst	32
4	Eosin Y as photocatalyst	13
5	Rhodamine 6G as photocatalyst	36
6	DCM as solvent	17
7	THF as solvent	0
8	DMF as solvent	0
9	2 mol% Acr^＋$\mathrm{MesClO}_{4}^{-}$	63
10	10 mol% Acr^＋$\mathrm{MesClO}_{4}^{-}$	80

Entry	Variation from the standard conditions	Yield^b/%
1	None	71 (63)
2	3CzClIPN as photocatalyst	53
3	Ir[dF(CF₃)ppy]₂(dtbpy)PF₆ as photocatalyst	32
4	Eosin Y as photocatalyst	13
5	Rhodamine 6G as photocatalyst	36
6	DCM as solvent	17
7	THF as solvent	0
8	DMF as solvent	0
9	2 mol% Acr^＋$\mathrm{MesClO}_{4}^{-}$	63
10	10 mol% Acr^＋$\mathrm{MesClO}_{4}^{-}$	80

可见光促进烯基硅化合物有氧氧化-叠氮化反应

Visible Light-Promoted Aerobic Oxo-azidation of Alkenyl Silanes

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Fig. & Tab. 5

References 23

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