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Copper-Catalyzed Microwave-Expedited Oxyphosphorylation of Alkynes with Diethyl Phosphite and t-Butyl Hydroperoxide Synthesis of Densely Functionalized Phosphonylated Indenones

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URI: http://hdl.handle.net/10498/33913

DOI: 10.1021/acs.joc.1c01763

ISSN: 1520-6904

ISSN: 0022-3263

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draft_Proof_JOC21.pdf (1.186Mb)
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Author/s
Macías Benítez, PabloAuthority UCA; Sierra Padilla, AlfonsoAuthority UCA; Jiménez Tenorio, ManuelAuthority UCA; Moreno Dorado, Francisco JavierAuthority UCA; Guerra Martínez, Francisco MiguelAuthority UCA
Date
2021
Department
Ciencia de los Materiales e Ingeniería Metalúrgica y Química Inorgánica; Química Analítica; Química Orgánica
Source
J. Org. Chem. 2021, 86, 16409−16424
Abstract
Treatment of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu(MeCN)4]BF4 under microwave irradiation produced the oxyphosphorylation of the triple bond, giving rise to the corresponding β-ketophosphonates in moderate-to-good yields. When the triple bond was conjugated to a carbonyl group bearing an aromatic ring, it led to the cyclization of the resulting ketone intermediate, producing eventually different phosphonylated indenones.
Subjects
copper; catalyzed; microwave; expedited; oxyphosphorylation; alkyne; phosphite; hydroperoxide; phosphonylated; indenone; preparation; derivatization
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  • Articulos Científicos Quim. Org. [327]
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
This work is under a Creative Commons License Attribution-NonCommercial-NoDerivatives 4.0 Internacional

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