122570-76-7Relevant articles and documents
A Protocol for the Ortho-Deuteration of Acidic Aromatic Compounds in D2O Catalyzed by Cationic RhIII
Garreau, Alyssa L.,Zhou, Hanyang,Young, Michael C.
supporting information, p. 7044 - 7048 (2019/09/30)
Methods to catalytically introduce deuterium in synthetically useful yields ortho to a carboxylic acid directing group on arenes typically requires D2 or high catalyst loadings, which makes using these approaches cost prohibitive for large-scale synthesis (equipment and reagent costs respectively). Herein, we present a simplified approach using low catalyst loadings of cationic RhIII and D2O as both deuterium source and solvent and show its application to H/D exchange on various carboxylic acid substrates.
ORGANIC CHEMISTRY IN WATER (PART V) NUCLEOPHILIC ADDITION OF WATER-SOLUBLE PHOSPHINES ON ACTIVATED ALKYNES: AN EFFICIENT SYNTHESIS OF NEW VINYLPHOSPHONIUM SALTS AND OF SPECIFICALLY DEUTERATED OLEFINS.
Larpent, Chantal,Meignan, Gerard,Patin, Henri
, p. 6381 - 6398 (2007/10/02)
Triphenylphosphine m-trisulfonate 1 and triphenylphosphine m-monosulfonate 2 react in water with activated alkynes R-CC-A (A = CO2H, CO2R1, COR2, CHO) affording new vinylphosphonium salts or vinylphosphine oxides or alkenes depending on the pH of the aqueous solution and on the nature of the substituent R.The reactions of 1 or 2 with alkynes bearing an electron-acceptor substituent R give rise to the corresponding trans disubstituted olefins.Specifically mono or dideuterated alkenes are thus obtained in good yields by sequential use of H2O-D2O.When R = H or Alkyl, vinylphosphonium salts or vinylphosphine oxides are quantitatively produced respectively in acidic or in neutral solution.
