41728-24-9Relevant academic research and scientific papers
The Cyclohexa-2,5-dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate
Chen, Weiqiang,Fang, Huaquan,Xie, Kaixue,Oestreich, Martin
supporting information, p. 15126 - 15129 (2020/10/23)
An aldehyde with a cyclohexa-2,5-dienyl group in the α-position is introduced as a storable surrogate of highly reactive acetaldehyde. The cyclohexa-2,5-dienyl unit is compatible with an enantioselective Michael addition to nitroalkenes promoted by a Haya
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.
