Tf <sub>2</sub> O-Mediated Phospha-Michael Addition to Unactivated α,β-Unsaturated Amides

Tf<sub>2</sub>O-mediated phospha-Michael addition to unactivated α,β-unsaturated amides has been developed under mild, metal-free conditions, providing efficient access to γ-aminophosphine oxides with excellent regioselectivity. This protocol features a broad substrate scope and good functional group tolerance, accommodating a range of electron-rich, electron-deficient, and base-sensitive groups such as methoxyl, nitro, cyano, ester, and carboxylic acid groups. Primary, secondary, and tertiary amides, as well as structurally complex acrylamides derived from bioactive molecules, are compatible, affording the phosphorylated amides in moderate to excellent yields.

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Publication Details

Journal
Organic Letters
Published
2025-12-04
DOI
https://doi.org/10.1021/acs.orglett.5c04353
Citations
1
Primary Topic
Advanced Synthetic Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.94
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Tf 2 O-Mediated Phospha-Michael Addition to Unactivated α,β-Unsaturated Amides

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1 citations
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Advanced Synthetic Organic Chemistry
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article

Tf 2 O-Mediated Phospha-Michael Addition to Unactivated α,β-Unsaturated Amides

Ju Wu, Yirui Shen, Ranran Zhu, Yufen Zhao, Tingting Xie
article en
1 citations

Abstract

Tf<sub>2</sub>O-mediated phospha-Michael addition to unactivated α,β-unsaturated amides has been developed under mild, metal-free conditions, providing efficient access to γ-aminophosphine oxides with excellent regioselectivity. This protocol features a broad substrate scope and good functional group tolerance, accommodating a range of electron-rich, electron-deficient, and base-sensitive groups such as methoxyl, nitro, cyano, ester, and carboxylic acid groups. Primary, secondary, and tertiary amides, as well as structurally complex acrylamides derived from bioactive molecules, are compatible, affording the phosphorylated amides in moderate to excellent yields.

Organic LettersVol. 27(50)
Ningbo University (CN), Ningbo University of Technology (CN), Drug Discovery Laboratory (Norway) (NO)
Openalex Percentile: Top 19%
Advanced Synthetic Organic Chemistry
0.94
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