Internally reuse by-product as promoter: A catalyst-free imine formation/Mukaiyama-Mannich sequence of α-amido sulfones with fluorinated silyl enol ethers

Xiao Si Hu; Jin Sheng Yu; Yi Gong; Jian Zhou

doi:10.1016/j.jfluchem.2019.01.003

Internally reuse by-product as promoter: A catalyst-free imine formation/Mukaiyama-Mannich sequence of α-amido sulfones with fluorinated silyl enol ethers

Xiao Si Hu
, Jin Sheng Yu^*
, Yi Gong
, Jian Zhou

^*此作品的通讯作者

化学与分子工程学院

East China Normal University
Guiyang University
CAS - Shanghai Institute of Organic Chemistry

科研成果: 期刊稿件 › 文章 › 同行评审

16 引用（Scopus）

摘要

Described herein is a catalyst-free tandem imine formation/Mukaiyama-Mannich sequence of fluorinated silyl enol ethers and α-amido sulfones, allowing the efficient synthesis of value-added β-amino α-fluorinated ketones in good to excellent yields. Noticeably, the key for high efficacy of the catalyst-free reaction is attributed to the in situ generated acidic by-product PhSO₂X (X = TMS or H) that can act as an promoter for the subsequent Mukaiyama-Mannich reaction.

源语言	英语
页（从-至）	106-114
页数	9
期刊	Journal of Fluorine Chemistry
卷	219
DOI	https://doi.org/10.1016/j.jfluchem.2019.01.003
出版状态	已出版 - 3月 2019

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@article{ab72cbbff0b14f4eb2e3e63e3d302fc6,

title = "Internally reuse by-product as promoter: A catalyst-free imine formation/Mukaiyama-Mannich sequence of α-amido sulfones with fluorinated silyl enol ethers",

abstract = "Described herein is a catalyst-free tandem imine formation/Mukaiyama-Mannich sequence of fluorinated silyl enol ethers and α-amido sulfones, allowing the efficient synthesis of value-added β-amino α-fluorinated ketones in good to excellent yields. Noticeably, the key for high efficacy of the catalyst-free reaction is attributed to the in situ generated acidic by-product PhSO2X (X = TMS or H) that can act as an promoter for the subsequent Mukaiyama-Mannich reaction.",

keywords = "Catalyst-free, Fluorinated enol silyl ethers, Mukaiyama-Mannich reaction, Reuse waste",

author = "Hu, \{Xiao Si\} and Yu, \{Jin Sheng\} and Yi Gong and Jian Zhou",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier B.V.",

year = "2019",

month = mar,

doi = "10.1016/j.jfluchem.2019.01.003",

language = "英语",

volume = "219",

pages = "106--114",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - Internally reuse by-product as promoter

T2 - A catalyst-free imine formation/Mukaiyama-Mannich sequence of α-amido sulfones with fluorinated silyl enol ethers

AU - Hu, Xiao Si

AU - Yu, Jin Sheng

AU - Gong, Yi

AU - Zhou, Jian

PY - 2019/3

Y1 - 2019/3

N2 - Described herein is a catalyst-free tandem imine formation/Mukaiyama-Mannich sequence of fluorinated silyl enol ethers and α-amido sulfones, allowing the efficient synthesis of value-added β-amino α-fluorinated ketones in good to excellent yields. Noticeably, the key for high efficacy of the catalyst-free reaction is attributed to the in situ generated acidic by-product PhSO2X (X = TMS or H) that can act as an promoter for the subsequent Mukaiyama-Mannich reaction.

AB - Described herein is a catalyst-free tandem imine formation/Mukaiyama-Mannich sequence of fluorinated silyl enol ethers and α-amido sulfones, allowing the efficient synthesis of value-added β-amino α-fluorinated ketones in good to excellent yields. Noticeably, the key for high efficacy of the catalyst-free reaction is attributed to the in situ generated acidic by-product PhSO2X (X = TMS or H) that can act as an promoter for the subsequent Mukaiyama-Mannich reaction.

KW - Catalyst-free

KW - Fluorinated enol silyl ethers

KW - Mukaiyama-Mannich reaction

KW - Reuse waste

UR - https://www.scopus.com/pages/publications/85060206856

U2 - 10.1016/j.jfluchem.2019.01.003

DO - 10.1016/j.jfluchem.2019.01.003

M3 - 文章

AN - SCOPUS:85060206856

SN - 0022-1139

VL - 219

SP - 106

EP - 114

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -

Internally reuse by-product as promoter: A catalyst-free imine formation/Mukaiyama-Mannich sequence of α-amido sulfones with fluorinated silyl enol ethers

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