Copper-Catalyzed Domino Phosphorylation/Cyclization of <i>ortho</i>-Alkynylketones for Accessing Phosphorylated 1<i>H</i>-Isochromenes

An effective and economical copper-catalyzed approach for the synthesis of phosphorylated 1<i>H</i>-isochromenes is reported. This method is the first example of focus on ketone phosphonylation to establish a C-P bond and 6-<i>endo</i>-<i>dig</i> cyclization to construct a C-O bond between aryl- and alkyl-substituted alkynylketones and H-phosphinate esters, H-phosphites, and H-phosphine oxides, resulting in chemo- and regioselective phosphorylated 1<i>H</i>-isochromenes with moderate to excellent yields under smooth reaction conditions.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-12-18
DOI
https://doi.org/10.1021/acs.joc.4c02239
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.25

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article

Copper-Catalyzed Domino Phosphorylation/Cyclization of ortho-Alkynylketones for Accessing Phosphorylated 1H-Isochromenes

Ya-Wen Xue, Xiaohong Wei, Xiaojun Yang, Shang‐Dong Yang et al.
1 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
0.25
article

Copper-Catalyzed Domino Phosphorylation/Cyclization of ortho-Alkynylketones for Accessing Phosphorylated 1H-Isochromenes

Ya-Wen Xue, Xiaohong Wei, Xiaojun Yang, Shang‐Dong Yang, Xiaohong Wang, Xuan Liu
article en
1 citations

Abstract

An effective and economical copper-catalyzed approach for the synthesis of phosphorylated 1<i>H</i>-isochromenes is reported. This method is the first example of focus on ketone phosphonylation to establish a C-P bond and 6-<i>endo</i>-<i>dig</i> cyclization to construct a C-O bond between aryl- and alkyl-substituted alkynylketones and H-phosphinate esters, H-phosphites, and H-phosphine oxides, resulting in chemo- and regioselective phosphorylated 1<i>H</i>-isochromenes with moderate to excellent yields under smooth reaction conditions.

The Journal of Organic ChemistryVol. 90(1)
State Ethnic Affairs Commission (CN), Lanzhou University (CN)
Natural Science Foundation of Gansu Province, Fundamental Research Funds for the Central Universities
Clean water and sanitation
Openalex Percentile: Top 45%
Catalytic C–H Functionalization Methods
0.25
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