Regioselective Intermolecular Hydroamidation of β-CF3-1,3-Enynamides: An Approach to Tri-Substituted γ-CF3-Allenamides

Yuxuan Cao; Zongxiang Yu; Yizhen Chen; Lu Liu; Yuanjing Xiao

doi:10.1002/ejoc.202400674

Regioselective Intermolecular Hydroamidation of β-CF₃-1,3-Enynamides: An Approach to Tri-Substituted γ-CF₃-Allenamides

Yuxuan Cao, Zongxiang Yu, Yizhen Chen, Lu Liu, Yuanjing Xiao

School of Chemistry and Molecular Engineering

East China Normal University

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

1 Scopus citations

Abstract

A simple base mediated, highly regioselective 1,4-hydroamidation of β-CF₃-1,3-enynamides with secondary amides for synthesis of tri-substituted γ-CF₃-allenamides compounds was developed. N-alkyl sulfonamides are generally good candidates for the present transformation. γ-CF₃-allenamides could be employed for synthesis of potential value-added compounds such as fluorinated halogenated pyrrole, tetrahydroquinoline and 2-CF₃-putrescine derivatives.

Original language	English
Article number	e202400674
Journal	European Journal of Organic Chemistry
Volume	27
Issue number	44
DOIs	https://doi.org/10.1002/ejoc.202400674
State	Published - 25 Nov 2024

Keywords

1,3-enynamides
Allenamides
Hydroamidation
Ynamides
γ-CF-allenamides

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10.1002/ejoc.202400674

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title = "Regioselective Intermolecular Hydroamidation of β-CF3-1,3-Enynamides: An Approach to Tri-Substituted γ-CF3-Allenamides",

abstract = "A simple base mediated, highly regioselective 1,4-hydroamidation of β-CF3-1,3-enynamides with secondary amides for synthesis of tri-substituted γ-CF3-allenamides compounds was developed. N-alkyl sulfonamides are generally good candidates for the present transformation. γ-CF3-allenamides could be employed for synthesis of potential value-added compounds such as fluorinated halogenated pyrrole, tetrahydroquinoline and 2-CF3-putrescine derivatives.",

keywords = "1,3-enynamides, Allenamides, Hydroamidation, Ynamides, γ-CF-allenamides",

author = "Yuxuan Cao and Zongxiang Yu and Yizhen Chen and Lu Liu and Yuanjing Xiao",

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T1 - Regioselective Intermolecular Hydroamidation of β-CF3-1,3-Enynamides

T2 - An Approach to Tri-Substituted γ-CF3-Allenamides

AU - Cao, Yuxuan

AU - Yu, Zongxiang

AU - Chen, Yizhen

AU - Liu, Lu

AU - Xiao, Yuanjing

PY - 2024/11/25

Y1 - 2024/11/25

N2 - A simple base mediated, highly regioselective 1,4-hydroamidation of β-CF3-1,3-enynamides with secondary amides for synthesis of tri-substituted γ-CF3-allenamides compounds was developed. N-alkyl sulfonamides are generally good candidates for the present transformation. γ-CF3-allenamides could be employed for synthesis of potential value-added compounds such as fluorinated halogenated pyrrole, tetrahydroquinoline and 2-CF3-putrescine derivatives.

AB - A simple base mediated, highly regioselective 1,4-hydroamidation of β-CF3-1,3-enynamides with secondary amides for synthesis of tri-substituted γ-CF3-allenamides compounds was developed. N-alkyl sulfonamides are generally good candidates for the present transformation. γ-CF3-allenamides could be employed for synthesis of potential value-added compounds such as fluorinated halogenated pyrrole, tetrahydroquinoline and 2-CF3-putrescine derivatives.

KW - 1,3-enynamides

KW - Allenamides

KW - Hydroamidation

KW - Ynamides

KW - γ-CF-allenamides

UR - https://www.scopus.com/pages/publications/85208413087

U2 - 10.1002/ejoc.202400674

DO - 10.1002/ejoc.202400674

M3 - 文章

AN - SCOPUS:85208413087

SN - 1434-193X

VL - 27

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 44

M1 - e202400674

ER -

Regioselective Intermolecular Hydroamidation of β-CF₃-1,3-Enynamides: An Approach to Tri-Substituted γ-CF₃-Allenamides

Abstract

Keywords

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