Enantioselective Synthesis of C2-Quaternary Indolin-3-ones by Pt-Catalyzed Alkynylation of 2-Aryl-3H-indol-3-one with Alkynylsilanes

Fan Yang; Shaojian Luo; Meifen Wang; Baomin Fan; Bo Yao

doi:10.1021/acs.joc.3c02807

Enantioselective Synthesis of C2-Quaternary Indolin-3-ones by Pt-Catalyzed Alkynylation of 2-Aryl-3H-indol-3-one with Alkynylsilanes

Fan Yang, Shaojian Luo, Meifen Wang, Baomin Fan^*, Bo Yao^*

^*此作品的通讯作者

化学与化工学院

科研成果: 期刊稿件 › 文章 › 同行评审

2 引用（Scopus）

摘要

An efficient method for the synthesis of five-membered chiral propargylic amines from 2-aryl-3H-indol-3-one and alkynylsilanes has been developed. The reaction proceeded under the catalytic system of PtCl₄, oxazoline-based ligand L11, Zn(CF₃COO)₂, and AcOH in DCE at 95 °C via in situ desilylation of TMS-alkynes. This methodology also highlights a new protocol for the in situ desilylation of alkynylsilanes. The reaction showed a broad substrate scope with good yields and enantioselectivity.

源语言	英语
页（从-至）	3359-3364
页数	6
期刊	Journal of Organic Chemistry
卷	89
期	5
DOI	https://doi.org/10.1021/acs.joc.3c02807
出版状态	已出版 - 1 3月 2024

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Yang, F., Luo, S., Wang, M., Fan, B., & Yao, B. (2024). Enantioselective Synthesis of C2-Quaternary Indolin-3-ones by Pt-Catalyzed Alkynylation of 2-Aryl-3H-indol-3-one with Alkynylsilanes. Journal of Organic Chemistry, 89(5), 3359-3364. https://doi.org/10.1021/acs.joc.3c02807

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abstract = "An efficient method for the synthesis of five-membered chiral propargylic amines from 2-aryl-3H-indol-3-one and alkynylsilanes has been developed. The reaction proceeded under the catalytic system of PtCl4, oxazoline-based ligand L11, Zn(CF3COO)2, and AcOH in DCE at 95 °C via in situ desilylation of TMS-alkynes. This methodology also highlights a new protocol for the in situ desilylation of alkynylsilanes. The reaction showed a broad substrate scope with good yields and enantioselectivity.",

author = "Fan Yang and Shaojian Luo and Meifen Wang and Baomin Fan and Bo Yao",

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T1 - Enantioselective Synthesis of C2-Quaternary Indolin-3-ones by Pt-Catalyzed Alkynylation of 2-Aryl-3H-indol-3-one with Alkynylsilanes

AU - Yang, Fan

AU - Luo, Shaojian

AU - Wang, Meifen

AU - Fan, Baomin

AU - Yao, Bo

PY - 2024/3/1

Y1 - 2024/3/1

N2 - An efficient method for the synthesis of five-membered chiral propargylic amines from 2-aryl-3H-indol-3-one and alkynylsilanes has been developed. The reaction proceeded under the catalytic system of PtCl4, oxazoline-based ligand L11, Zn(CF3COO)2, and AcOH in DCE at 95 °C via in situ desilylation of TMS-alkynes. This methodology also highlights a new protocol for the in situ desilylation of alkynylsilanes. The reaction showed a broad substrate scope with good yields and enantioselectivity.

AB - An efficient method for the synthesis of five-membered chiral propargylic amines from 2-aryl-3H-indol-3-one and alkynylsilanes has been developed. The reaction proceeded under the catalytic system of PtCl4, oxazoline-based ligand L11, Zn(CF3COO)2, and AcOH in DCE at 95 °C via in situ desilylation of TMS-alkynes. This methodology also highlights a new protocol for the in situ desilylation of alkynylsilanes. The reaction showed a broad substrate scope with good yields and enantioselectivity.

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JO - Journal of Organic Chemistry

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Enantioselective Synthesis of C2-Quaternary Indolin-3-ones by Pt-Catalyzed Alkynylation of 2-Aryl-3H-indol-3-one with Alkynylsilanes

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