Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles

doi:10.6023/cjoc202401010

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 1786-1792.DOI: 10.6023/cjoc202401010 Previous Articles Next Articles

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邻炔基苯胺氢胺化合成轴手性吲哚研究进展

王家晟^a,†, 王泽树^b,†, 何卫民^a^,^*(), 叶龙武^a^,^b^,^c^,^*()

a 南华大学化学化工学院湖南衡阳 421001
b 厦门大学化学化工学院福建厦门 361005
c 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2024-01-12 修回日期:2024-02-23 发布日期:2024-03-12
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(22125108); 湖南省科技创新计划(2023RC4004)

Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles

Jiasheng Wang^a,†, Zeshu Wang^b,†, Weimin He^a,*(), Longwu Ye^a^,^b^,^c,*()

a College of Chemistry and Chemical Engineering, Nanhua University, Hengyang, Hunan 421001
b College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2024-01-12 Revised:2024-02-23 Published:2024-03-12
Contact: * E-mail: weiminhe@usc.edu.cn; longwuye@xmu.edu.cn
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22125108); Science and Technology Innovation Program of Hunan Province(2023RC4004)

Hydroamination of o-alkynylanilines is an important approach for the synthesis of indoles. On this basis, o-alkynylanilines bearing substituents with certain steric hindrance could undergo chiral transition-metal catalyzed or organocatalytic atroposelective 5-endo-dig cyclolization for the synthesis of axially chiral indoles. Classified by the types of chiral axes in the products of enantioselective hydroamination, the catalytic enantioselective methods for the preparation of axially chiral indoles containing C—N, C—C and N—N chiral axes are systematically introduced.

Key words: asymmetric catalysis, hydroamination reaction, axially chiral indole, alkyne

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Jiasheng Wang, Zeshu Wang, Weimin He, Longwu Ye. Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1786-1792.

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Fig. & Tab. 10

Figure 1. Axially chiral indole-based skeletons in natural products and chiral catalysts and ligands

Scheme 1. Hydroamination of o-alkynylanilines for the synthesis of axially chiral indoles

Scheme 2. Palladium-catalyzed hydroamination of o-alkynyl- anilines for the synthesis of C—N axially chiral indoles

Scheme 3. Chiral Br?nsted acid-catalyzed hydroamination of ynamides for the synthesis of C—N axially chiral indoles

Scheme 4. Organocatalytic hydroamination of o-alkynylanilines for the synthesis of C—C axially chiral indoles

Scheme 5. Silver-catalyzed hydroamination of o-alkynylanilines for the synthesis of C—C axially chiral indoles

Scheme 6. Palladium-catalyzed hydroamination of o-alkynyl- anilines for the synthesis of N—N axially chiral indoles

Scheme 7. Chiral Br?nsted acid-catalyzed hydroamination of o-alkynylanilines for synthesis of N—N axially chiral indoles

Scheme 8. Asymmetric hydroamination of o-alkynylanilines for the synthesis of C—N, C—C and N—N axially chiral indoles

Scheme 9. Applications of axially chiral indoles synthesized from the hydroamination of o-alkynylanilines in asymmetric catalysis (Zhao, C.)

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邻炔基苯胺氢胺化合成轴手性吲哚研究进展

Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles

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