5717-41-9Relevant articles and documents
A Short Synthesis of Allene- and Cumulenecarboxylates
Kohl-Mines, Elisabeth,Hansen, Hans-Juergen
, p. 2244 - 2248 (1985)
It is shown that carboxylic acids, in the presence of Bu3N and 2-chloro-1-methylpyridinium iodide in toluene or CH2Cl2, react with phosphoranes to yield the corresponding esters of allene carboxylic acids (cf.Scheme
Metal-Free Transfer Hydroiodination of C-C Multiple Bonds
Chen, Weiqiang,Walker, Johannes C. L.,Oestreich, Martin
supporting information, p. 1135 - 1140 (2019/01/11)
The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Br?nsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove volatile waste. This hydroiodination reaction avoids precarious handling of hydrogen iodide or hydroiodic acid. By this, a broad range of previously unknown or difficult-to-prepare vinyl iodides can be accessed in stereocontrolled fashion.
Nickel-catalyzed, ligand-free, diastereoselective synthesis of 3-methyleneindan-1-ols
Panchal, Heena,Clarke, Christopher,Bell, Charles,Karad, Somnath Narayan,Lewis, William,Lam, Hon Wai
supporting information, p. 12389 - 12392 (2018/11/20)
Nickel-catalyzed, highly diastereoselective annulations between activated allenes and 2-acetylarylboronic acid or 2-formylarylboronic acids are reported. No ligand for nickel is required, and the reactions proceed efficiently at room temperature to give a broad range of substituted 3-methyleneindan-1-ols. Preliminary results of an enantioselective variant are also described.
