Hydroboration of unsaturated phosphonic esters: synthesis of boronophosphonates and trisubstituted vinylphosphonates.
[figure: see text] Hydroboration of vinyl phosphonates with pinacolborane (PBH) proceeds to give phosphonoboronates, 2. Surprisingly, such compounds have not been reported before. The reaction works well with terminal alkenylphosphonates. Internal alkenylphosphonates give complex mixtures. Hydroboration/Suzuki coupling of alkynylphosphonates, with PBH, in a one-pot procedure gives trisubstituted vinylphosphonates in good overall yields and provides a new synthesis of these compounds.
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Department of Medicinal Chemistry and Natural Products, School of Pharmacy, Hebrew University in Jerusalem, 91120 Israel.
Srebnik
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D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D007202:Indicators and Reagents; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014753:Vinyl Compounds
D001896:Boron Compounds; D007202:Indicators and Reagents; D009943:Organophosphorus Compounds; D014753:Vinyl Compounds