利用可见光引发1,6-烯炔的增环酰化双官能化制备1-茚酮衍生物

doi:10.6023/cjoc202407040

有机化学 ›› 2025, Vol. 45 ›› Issue (5): 1729-1738.DOI: 10.6023/cjoc202407040 上一篇下一篇

研究论文

利用可见光引发1,6-烯炔的增环酰化双官能化制备1-茚酮衍生物

林风^a^,^b^,^†, 张艳^b^,^†, 吴明^b, 刘会艳^b^,^*(), 郝文娟^b, 姜波^a^,^b^,^*()

^a 江苏师范大学敬文书院江苏徐州 221116
^b 江苏师范大学化学与材料科学学院江苏徐州 221116

收稿日期:2024-07-26 修回日期:2024-10-03 发布日期:2024-11-08
作者简介:
^†共同第一作者.
基金资助:
国家自然科学基金(22271123); 国家级大学生创新创业训练计划(202310320033Z)

Visible-Light-Induced Annulative Acylative Difunctionalization of 1,6-Enynes for Accessing 1-Indanones

Feng Lin^a^,^b^,^†, Yan Zhang^b^,^†, Ming Wu^b, Huiyan Liu^b^,^*(), Wen-Juan Hao^b, Bo Jiang^a^,^b^,^*()

^a C.W. Chu College, Jiangsu Normal University, Xuzhou, Jiangsu 221116
^b School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116

Received:2024-07-26 Revised:2024-10-03 Published:2024-11-08
Contact: * E-mail: liuhuiyan72@163.com; jiangchem@jsnu.edu.cn
About author:
^†The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22271123); National College Students’ Innovation and Entrepreneurship Training Program(202310320033Z)

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摘要/Abstract

报道了一种新型光催化1,6-烯炔参与的增环酰化-双官能化反应, 立体选择性地合成具有环季碳中心的酰基取代1-茚酮衍生物, 收率中等至良好. 该光催化反应通过调整酰基自由基前体类型, 实现了不饱和烃的两类酰化官能化反应. 当使用芳酰氯为双官能团试剂时, 其与1,6-烯炔发生增环氯酰化反应; 而使用酰基肟酯作为酰基自由基前体时, 与醇和1,6-烯炔发生三组分增环烷氧基化酰化反应. 目前方法展现出良好官能团相容性、广泛底物范围和温和反应条件.

关键词: 可见光催化反应, 增环氯酰化反应, 增环烷氧基化酰化反应, 1,6-烯炔衍生物

A new photocatalytic annulative acylative difunctionalization of 1,6-enynes is reported, enabling stereoselective access to acylated 1-indanones with cyclic quaternary centers in moderate to good yields. This photocatalysis enables two types of acylation of unsaturated hydrocarbons by adjusting the categories of acyl radical precursors. Aroyl chlorides as bifunctional reagents react with 1,6-enynes to realize annulative chloroacylation, while acyl oxime esters are used as acyl radical precursors, which undergo a three-component annulative alkoxyacylation by treatment with 1,6-enynes and alcohols. The current method demonstrates good functional group compatibility, a broad substrate scope and mild reaction conditions

Key words: photoredox catalysis, annulative chloroacylation, annulative alkoxyacylation, 1,6-enynes

引用此文

林风, 张艳, 吴明, 刘会艳, 郝文娟, 姜波. 利用可见光引发1,6-烯炔的增环酰化双官能化制备1-茚酮衍生物[J]. 有机化学, 2025, 45(5): 1729-1738.

Feng Lin, Yan Zhang, Ming Wu, Huiyan Liu, Wen-Juan Hao, Bo Jiang. Visible-Light-Induced Annulative Acylative Difunctionalization of 1,6-Enynes for Accessing 1-Indanones[J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1729-1738.

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Entry	Variation of the established conditions	Yield^b/%
1	None	85
2	1.0 mol% fac-Ir(ppy)₃	77
3	5.0 mol% fac-Ir(ppy)₃	85
4	2,4,6-Collidine (20 mol%) as the base	30
5	2,6-Lutidine (20 mol%) as the base	45
6	DMAP (20 mol%) as the base	0
7	2,6-Dichloropyridine (10 mol%)	56
8	THF instead of EtOAc	NR
9	In the air	Trace
10	Ru(bpy)₃Cl₂•6H₂O instead of fac-Ir(ppy)₃	Trace
11	Without fac-Ir(ppy)₃	0
12	No light	0

Entry	Variation of the established conditions	Yield^b/%
1	None	85
2	1.0 mol% fac-Ir(ppy)₃	77
3	5.0 mol% fac-Ir(ppy)₃	85
4	2,4,6-Collidine (20 mol%) as the base	30
5	2,6-Lutidine (20 mol%) as the base	45
6	DMAP (20 mol%) as the base	0
7	2,6-Dichloropyridine (10 mol%)	56
8	THF instead of EtOAc	NR
9	In the air	Trace
10	Ru(bpy)₃Cl₂•6H₂O instead of fac-Ir(ppy)₃	Trace
11	Without fac-Ir(ppy)₃	0
12	No light	0

Entry	Variation of the established conditions	Yield^b/%
1	None	45
2	1.0 mol% of fac-Ir(ppy)₃	45
3	1.0 mol% of fac-Ir(ppy)₃ without base	65
4	EtOH instead of MeOH	Trace
5	K₂CO₃ (2.0 equiv.)	21
6	Na₂CO₃ (2.0 equiv.)	53
7	Eosin Y instead of fac-Ir(ppy)₃	32
8	Ru(bpy)₃Cl₂•6H₂O instead of fac-Ir(ppy)₃	Trace
9	In the air	55
10	Without fac-Ir(ppy)₃	0
11	No light	0

Entry	Variation of the established conditions	Yield^b/%
1	None	45
2	1.0 mol% of fac-Ir(ppy)₃	45
3	1.0 mol% of fac-Ir(ppy)₃ without base	65
4	EtOH instead of MeOH	Trace
5	K₂CO₃ (2.0 equiv.)	21
6	Na₂CO₃ (2.0 equiv.)	53
7	Eosin Y instead of fac-Ir(ppy)₃	32
8	Ru(bpy)₃Cl₂•6H₂O instead of fac-Ir(ppy)₃	Trace
9	In the air	55
10	Without fac-Ir(ppy)₃	0
11	No light	0

利用可见光引发1,6-烯炔的增环酰化双官能化制备1-茚酮衍生物

Visible-Light-Induced Annulative Acylative Difunctionalization of 1,6-Enynes for Accessing 1-Indanones

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