Organic Letters
Organic Letters
5 years ago

Tuning the Catalyst Reactivity of Imidazolylidene Catalysts through Substituent Effects on the N-Aryl Groups

Tuning the Catalyst Reactivity of Imidazolylidene Catalysts through Substituent Effects on the N-Aryl Groups
Nobuyuki Mase, Naoharu Watanabe, Kohei Sato, Tetsuo Narumi, Ryuji Kyan
A series of imidazolium salts with various N-aryl groups were synthesized, and their catalytic activities were evaluated to investigate the contribution of the N-aryl groups to the catalytic activity in the synthesis of γ-butyrolactone through an a3→d3-umpolung addition. Imidazolylidenes with 2,6-diethylphenyl groups were effective catalysts, and several mechanistic studies, including a deuterium kinetic isotope effect study, revealed that both steric and kinetic effects were responsible for the enhanced catalytic activity.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01105

DOI: 10.1021/acs.orglett.7b01105

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.