Jump to main content
Jump to site search

Issue 48, 2019
Previous Article Next Article

Copper-catalysed, diboron-mediated cis-dideuterated semihydrogenation of alkynes with heavy water

Author affiliations

Abstract

Methods to incorporate deuterium atoms into organic molecules are valuable for the pharmaceutical industry. Here, we found that diboron reagents can efficiently mediate the transfer of two D atoms from heavy water directly onto alkynes through copper-catalysed cis-selective semihydrogenation. Avoiding the use of costly and flammable D2 gas, this safe and practical process can proceed with excellent chemoselectivity and stereoselectivity. Utilizing the present method as the key step, the formal asymmetric total synthesis of d2-deuterium-labeled cis-combretastatin A4 is demonstrated. Mechanistic studies suggest that monoborylation of alkynes is the key step for this semihydrogenation process.

Graphical abstract: Copper-catalysed, diboron-mediated cis-dideuterated semihydrogenation of alkynes with heavy water

Back to tab navigation

Supplementary files

Publication details

The article was received on 26 Apr 2019, accepted on 21 May 2019 and first published on 21 May 2019


Article type: Communication
DOI: 10.1039/C9CC03213D
Chem. Commun., 2019,55, 6922-6925

  •   Request permissions

    Copper-catalysed, diboron-mediated cis-dideuterated semihydrogenation of alkynes with heavy water

    X. Han, J. Hu, C. Chen, Y. Yuan and Z. Shi, Chem. Commun., 2019, 55, 6922
    DOI: 10.1039/C9CC03213D

Search articles by author

Spotlight

Advertisements