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Volumn , Issue 12, 2007, Pages 1863-1868

A facile anchoring of the bisphosphonate moiety into alcohols and phenols through copper carbenoid mediated O-H insertion reaction

(2) Lecerclé, Delphine a Taran, Frédéric a

a SERVICE DE CHIMIE BIOORGANIQUE ET DE MARQUAGE (France)

Author keywords

Carbenoids; Copper; Insertions; Phosphorus; Rhodium

Indexed keywords

ALCOHOL; BISPHOSPHONIC ACID DERIVATIVE; CARBENOID; COPPER CARBENOID; PHENOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 34547676275 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-984535 Document Type: Article

Times cited : (8)

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- General Procedure To a solution of diazo bisphosphonate 1a (100 mg, 0.318 mmol) and alcohol (0.350 mmol) in 6 mL of anhyd toluene was added Cu(OTf)2 (1.2 mg, 0.003 mmol, The mixture was heated under reflux for 8 or 12 h and then evaporated under reduced pressure. The residue was purified directly by flash chromatography on silica column (acetone-CH 2Cl2, 1:1) to afford the desired product. All new compounds have been characterized by 1H NMR, 13C NMR, 31P NMR, IR, and mass spectroscopy. Selected Data: Compound 5b: 1H NMR (400 MHz, CDCl3, δ, 1.29 (t, J, 7.2 Hz, 6 H, 1.31 (t, J, 7.2 Hz, 6H, 4.04 (t, J, 17.8 Hz, 1 H, 4.08-4.20 (m, 8 H, 4.80 (s, 2 H, 7.26-7.38 (m, 5 H)ppm. 13C NMR (100 MHz, CDCl3, δ, 16.32-1641 (m, 63.16 (d, J, 3.0 Hz, 63.19 (d, J, 3.0 Hz, 63.31 d, J, 3.0 Hz, 63.34
- 3): δ = 16.30-16.35 (m), 39.03, 51.68, 63.18-63.32 (m), 71.97 (t, J = 4.5 Hz), 73.53 ...

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