72946-20-4Relevant academic research and scientific papers
Synthesis of furan-3-carboxylic and 4-methylene-4,5-dihydrofuran-3- carboxylic esters by direct palladium iodide catalyzed oxidative carbonylation of 3-yne-1,2-diol derivatives
Gabriele, Bartolo,Mancuso, Raffaella,Maltese, Vito,Veltri, Lucia,Salerno, Giuseppe
, p. 8657 - 8668 (2012/11/07)
A variety of 3-yne-1,2-diol derivatives 1, bearing a primary or secondary alcoholic group at C-1, have been efficiently converted into high value added furan-3-carboxylic esters 2 in one step by PdI2/KI-catalyzed direct oxidative carbonylation, carried out in alcoholic media under relatively mild conditions (100 °C under 40 atm of a 4/1 mixture of CO and air). Carbonylated furans 2 were obtained in fair to excellent isolated yields (56-93%) through a sequential 5-endo-dig heterocyclization-alkoxycarbonylation- dehydration process, using only oxygen as the external oxidant. Under similar conditions, 2-methyl-3-yne-1,2-diols 3, bearing a tertiary alcoholic group, afforded 4-methylene-4,5-dihydrofuran-3-carboxylates 4 in satisfactory yields (58-70%).
Cationic gold(I)-mediated intramolecular cyclization of 3-alkyne-1,2-diols and 1-amino-3-alkyn-2-ols: A practical route to furans and pyrroles
Egi, Masahiro,Azechi, Kenji,Akai, Shuji
supporting information; experimental part, p. 5002 - 5005 (2009/12/26)
The intramolecular cyclizations of the 3-alkyne-1,2-diols and the 1-amlno-3-alkyn-2-ols with a low catalyst loading (0.05-0.5 mol %) of (Ph 3P)AuCl - AgNTf2 or (Ph3P)AuCl-AgOTf proceeded at room temperature to provide a variety of substituted furans and pyrroles In excellent yields (85-98% yields). This method Is also fully applicable to the conversion of several dozen grams of the substrate using only 0.05 mol % each of the Au and Ag catalysts.
Practical alternatives for the synthesis of β-iodofurans by 5-endo-dig cyclisations of 3-alkyne-1,2-diols
El-Taeb, Gamila M.M.,Evans, Ann B.,Jones, Simon,Knight, David W.
, p. 5945 - 5948 (2007/10/03)
Iodocyclisations of 3-alkyne-1,2-diols, obtained from acetylides and α-hydroxy-ketones or esters, give generally excellent yields of β-iodofurans by 5-endo-dig cyclisation followed by dehydration.
