Rhodium(III)-Catalyzed Annulative Coupling between Sulfoxonium Ylides and Diazo Compounds

doi:10.6023/cjoc202405011

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (1): 331-342.DOI: 10.6023/cjoc202405011 Previous Articles Next Articles

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铑(III)催化氧化锍叶立德和重氮化合物环化偶联反应

杨帆^a, 范小梦^a, 姚雪婧^b, 米瑞杰^b^,^*(), 于松杰^b^,^*(), 李兴伟^b^,^*(), 肖建^a^,^*()

a 青岛农业大学化学与药学院山东青岛 226109
b 山东大学化学与化工学院前沿化学研究院山东青岛 266237

收稿日期:2024-05-10 修回日期:2024-06-16 发布日期:2024-07-17
作者简介:
†共同第一作者
基金资助:
山东省泰山学者建设(tsqn201909131)

Rhodium(III)-Catalyzed Annulative Coupling between Sulfoxonium Ylides and Diazo Compounds

Fan Yang^a, Xiaomeng Fan^a, Xuejing Yao^b, Ruijie Mi^b(), Songjie Yu^b(), Xingwei Li^b(), Jian Xiao^a()

a College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao, Shandong 266109
b Institute of Frontier Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Qingdao, Shandong 266237

Received:2024-05-10 Revised:2024-06-16 Published:2024-07-17
Contact: *E-mail: 202290900001@sdu.edu.cn; chemjianxiao@163.com; yusongjie08@mails.ucas.ac.cn; lixw@snnu.edu.cn
About author:
†These authors contributed equally to this work.
Supported by:
Taishan Scholars Construction Projects of Shandong Province(tsqn201909131)

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Abstract

The Rh(III)-catalyzed C—H functionalization of sulfoxonium ylides and successively annulation with two classes of cyclic diazo compounds has been realized, affording structurally diverse fused-ring or spirocyclic compounds under redox- neutral conditions. The reaction proceeds via successive chelation-assisted C—H activation, carbene insertion, and intra- molecular [3 ＋ 3]/[4 ＋ 1] annulation processes.

Key words: rhodium catalysis, sulfoxonium ylide, C—H activation, diazo compound, annulation

Cite this article

Fan Yang, Xiaomeng Fan, Xuejing Yao, Ruijie Mi, Songjie Yu, Xingwei Li, Jian Xiao. Rhodium(III)-Catalyzed Annulative Coupling between Sulfoxonium Ylides and Diazo Compounds[J]. Chinese Journal of Organic Chemistry, 2025, 45(1): 331-342.

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Fig. & Tab. 8

Scheme 1. Rhodium(III)-catalyzed sulfoxonium ylide directed C—H activation/annulation

Entry	Solvent	Temp./℃	Additive	Yield^b/%
1	DCM	60	AcOH	70
2	DCE	60	AcOH	75
3 4 5 6 7 8 9 10 11 12 13 14^d	Toluene TFE MeOH THF THF THF THF THF THF THF THF THF	60 60 60 60 60 60 60 60 60 60 40 80	AcOH AcOH AcOH AcOH NaOAc Zn(OAc)₂ PhCO₂H 1-AdCO₂H MesCO₂H PivOH PivOH PivOH	53 49 62 79 Trace 53 80 79 67 88 (86)^c 65 82

Table 1. Optimization studiesa

Table 2. Scope of [3＋3] annulationa,b

Table 3. Scope of [4＋1] spiro annulationa,b

Scheme 2. Large-scale reaction and derivatization of coupled products

Scheme 3. Mechanistic studies

Scheme 4. Proposed mechanism of [4＋1] spiro annulation

Scheme 5. Proposed mechanism of [3＋3] annulation

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铑(III)催化氧化锍叶立德和重氮化合物环化偶联反应

Rhodium(III)-Catalyzed Annulative Coupling between Sulfoxonium Ylides and Diazo Compounds

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Fig. & Tab. 8

References 17

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