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Published on: January 17, 2020
Metal-Free Transfer Hydroiodination of C-C Multiple Bonds
Weiqiang Chen1, Johannes C L Walker1, Martin Oestreich1
1Institut für Chemie , Technische Universität Berlin , Strasse des 17. Juni 115 , 10623 Berlin , Germany.
Abstract:
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 Brønsted 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.
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