Pd/Novel Axially Chiral Phosphine-Alkene Ligands Catalyzed Asymmetric Allylic Alkylation of Indoles

doi:10.6023/cjoc202209002

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (10): 3373-3381.DOI: 10.6023/cjoc202209002 Previous Articles Next Articles

Special Issue: 不对称催化专辑

ARTICLES

钯/新型轴手性膦-烯配体催化的吲哚不对称烯丙基烷基化反应

贾仕虎^a, 陈思元^a, 刘泽水^a^,^b, 程鸿刚^a^,^*(), 周强辉^a^,^c^,^*()

a 武汉大学化学与分子科学学院武汉 430072
b 郑州大学化学学院绿色催化中心郑州 450001
c 武汉大学高等研究院武汉 430072

收稿日期:2022-09-01 修回日期:2022-10-11 发布日期:2022-11-02
通讯作者: 程鸿刚, 周强辉
基金资助:
国家自然科学基金(21871213); 国家自然科学基金(22071189); 中央大学基础研究基金(2042021kf0214)

Pd/Novel Axially Chiral Phosphine-Alkene Ligands Catalyzed Asymmetric Allylic Alkylation of Indoles

Shihu Jia^a, Siyuan Chen^a, Zeshui Liu^a^,^b, Honggang Cheng^a(), Qianghui Zhou^a^,^c()

a College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
b Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001
c The Institute for Advanced Studies, Wuhan University, Wuhan 430072

Received:2022-09-01 Revised:2022-10-11 Published:2022-11-02
Contact: Honggang Cheng, Qianghui Zhou
Supported by:
National Natural Science Foundation of China(21871213); National Natural Science Foundation of China(22071189); Fundamental Research Funds for Central Universities(2042021kf0214)

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Abstract

A new type of axially chiral phosphine-alkene ligands have been developed via a two-step modular synthesis for Pd-catalyzed asymmetric allylic alkylation of indoles. Under optimized reaction conditions, a series of chiral allylindole products were obtained in generally high yields (up to 95%) and excellent enantioselectivities (up to 96% ee).

Key words: palladium catalysis, phosphine-alkene ligand, indole, allylic alkylation, asymmetric catalysis

Cite this article

Shihu Jia, Siyuan Chen, Zeshui Liu, Honggang Cheng, Qianghui Zhou. Pd/Novel Axially Chiral Phosphine-Alkene Ligands Catalyzed Asymmetric Allylic Alkylation of Indoles[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3373-3381.

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Fig. & Tab. 6

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Entry	Ligand	Yield^b/%	ee^c/%
1	8a	92	11
2	8b	91	93
3	8c	85	50
4	8d	91	94
5	8e	75	70

Entry	Ligand	Yield^b/%	ee^c/%
1	8a	92	11
2	8b	91	93
3	8c	85	50
4	8d	91	94
5	8e	75	70

Entry	Base	Solvent	Time/h	Yield^b/%	ee^c/%
1	K₂CO₃	CH₂Cl₂	24	91	94
2	Cs₂CO₃	CH₂Cl₂	24	95	96
3	Na₂CO₃	CH₂Cl₂	24	Trace	Trace
4	Li₂CO₃	CH₂Cl₂	24	Trace	Trace
5	Et₃N	CH₂Cl₂	24	Trace	Trace
6	Cs₂CO₃	CH₂Cl₂	12	92	96
7	Cs₂CO₃	CH₂Cl₂	18	95 (95^d)	96
8	Cs₂CO₃	Toluene	18	67	91
9	Cs₂CO₃	THF	18	30	75

Entry	Base	Solvent	Time/h	Yield^b/%	ee^c/%
1	K₂CO₃	CH₂Cl₂	24	91	94
2	Cs₂CO₃	CH₂Cl₂	24	95	96
3	Na₂CO₃	CH₂Cl₂	24	Trace	Trace
4	Li₂CO₃	CH₂Cl₂	24	Trace	Trace
5	Et₃N	CH₂Cl₂	24	Trace	Trace
6	Cs₂CO₃	CH₂Cl₂	12	92	96
7	Cs₂CO₃	CH₂Cl₂	18	95 (95^d)	96
8	Cs₂CO₃	Toluene	18	67	91
9	Cs₂CO₃	THF	18	30	75

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钯/新型轴手性膦-烯配体催化的吲哚不对称烯丙基烷基化反应

Pd/Novel Axially Chiral Phosphine-Alkene Ligands Catalyzed Asymmetric Allylic Alkylation of Indoles

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