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

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

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

16 Scopus citations

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.

Original language	English
Pages (from-to)	106-114
Number of pages	9
Journal	Journal of Fluorine Chemistry
Volume	219
DOIs	https://doi.org/10.1016/j.jfluchem.2019.01.003
State	Published - Mar 2019

Keywords

Catalyst-free
Fluorinated enol silyl ethers
Mukaiyama-Mannich reaction
Reuse waste

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10.1016/j.jfluchem.2019.01.003

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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.",

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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

Abstract

Keywords

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