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^*

^*Corresponding author for this work

Yunnan Minzu University

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3359-3364
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	89
Issue number	5
DOIs	https://doi.org/10.1021/acs.joc.3c02807
Publication status	Published - 1 Mar 2024

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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",

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

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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.

UR - https://www.scopus.com/pages/publications/85186090572

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

Abstract

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