Iridium-Catalyzed Hydrosilylation of Alkynes

  • Author:
  • Published: 04 September 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Communications Chemistry/Springer Nature Limited
thumbnail image: Iridium-Catalyzed Hydrosilylation of Alkynes

Vinylsilanes are useful intermediates in organic synthesis. They can be prepared, e.g., by the hydrosilylation of alkynes. There are several methods for the synthesis of β-vinylsilanes, while paths to α-vinylsilanes are rarer. Some of the existing methods for the synthesis of α-vinylsilanes suffer from unstable or expensive catalysts, which hampers their industrial application.

Shengtao Ding, Beijing University of Chemical Technology, China, and colleagues have developed an iridium-catalyzed hydrosilylation of terminal alkynes with α-regioselectivity. The team used the simple catalyst [Ir(μ-Cl)(cod)]2 (cod = 1,5-cyclooctadiene) and the bulky trimethylsilyl-protected trihydroxysilane (TMSO)3SiH to convert a variety of terminal alkynes to α-vinylsilanes (pictured) in acetonitrile at room temperature.

The reaction proceeds with good regio- and stereoselectivity and provides high yields. According to the team, it is the first iridium-catalyzed hydrosilylation of terminal alkynes with excellent α-selectivity. The (TMSO)3Si group can be converted into other useful silyl groups.


Article Views: 1230

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH