Silicon‐Mediated Synthesis of Acetamides

  • ChemPubSoc Europe Logo
  • Author: Angewandte Chemie International Edition
  • Published Date: 15 July 2019
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Silicon‐Mediated Synthesis of Acetamides

The activation and coupling of small molecules is a useful strategy for the synthesis of organic commodities (hydrocarbons, alcohols, ketones, or carbonic acids) and fine chemicals. One example for this is the bottom-up synthesis of heteroatom-containing organic molecules such as amines, amides, or cyanides from carbon oxides and ammonia as simple building blocks.


Matthias Driess and colleagues, Technische Universität Berlin, Germany, have developed a silicon-mediated direct coupling of carbon monoxide, ammonia, and primary amines to form acetamides. The transformation starts with the deoxygenative homocoupling of two CO molecules at two cooperative divalent silicon atoms in a bis(silylene) (pictured above). Ammonolysis of the resulting disilaketene (pictured below on the left) first causes the formation of an N-silylated carboxamide and then affords the desired acetamide and disilyldiamide.


According to the researchers, this work could inspire the further development of coupling reactions of small molecules based on earth-crust-abundant, "green" elements such as silicon.


 

Article Views: 1008

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

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH