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

Yunnan Minzu University

科研成果: 期刊稿件 › 文章 › 同行评审

1 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

访问文件

10.1021/acs.joc.3c02807

其它文件与链接

链接到 Scopus 的出版物

引用此

@article{6b14fe0af5b84b1b9161e355134f756f,

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

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",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society",

year = "2024",

month = mar,

day = "1",

doi = "10.1021/acs.joc.3c02807",

language = "English",

volume = "89",

pages = "3359--3364",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=85186090572&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.3c02807

DO - 10.1021/acs.joc.3c02807

M3 - Article

AN - SCOPUS:85186090572

SN - 0022-3263

VL - 89

SP - 3359

EP - 3364

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

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

摘要

访问文件

其它文件与链接

指纹

引用此