Selective Synthesis of o-Acylbenzylphosphonates by Insertion Reactions of Arynes into β-Ketophosphonates

Selective Synthesis of o-Acylbenzylphosphonates by Insertion Reactions of Arynes into β-Ketophosphonates

A mild method for selective synthesis of o-acylbenzylphosphonates has been developed by the reactions of arynes with β-ketophosphonates. In the presence of CsF and THF, the carbon−carbon σ-bonds of 2-oxopropylphosphonates were selectively cleaved and added to arynes providing the corresponding 2-acy...

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Veröffentlicht in:Journal of organic chemistry 2009-08, Vol.74 (15), p.5691-5694
Hauptverfasser: Liu, Yi-Lin, Liang, Yun, Pi, Shao-Feng, Li, Jin-Heng
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Chemistry
Exact sciences and technology
Hydrocarbons, Aromatic - chemical synthesis
Hydrocarbons, Aromatic - chemistry
Molecular Structure
Organic chemistry
Organometalloidal and organometallic compounds
Organophosphonates - chemical synthesis
Organophosphonates - chemistry
P derivatives
Preparations and properties
Stereoisomerism
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Beschreibung
Zusammenfassung:A mild method for selective synthesis of o-acylbenzylphosphonates has been developed by the reactions of arynes with β-ketophosphonates. In the presence of CsF and THF, the carbon−carbon σ-bonds of 2-oxopropylphosphonates were selectively cleaved and added to arynes providing the corresponding 2-acylbenzylphosphonates in moderate to good yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo900847u