Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Transition Metal-Free α-Csp3-H Methylenation of Ketones to Form CC Bond Using Dimethyl Sulfoxide as Carbon Source

Transition Metal-Free α-Csp3-H Methylenation of Ketones to Form CC Bond Using Dimethyl Sulfoxide as Carbon Source
Yu-Qun Hu, Peng-Yi Ji, Qiang Liu, Yu-Feng Liu, Can-Cheng Guo, Jing-Wen Xu, Wei-Ping Luo
A direct α-Csp3-H methylenation of arylketones to form C═C bond using dimethyl sulfoxide as one-carbon source is achieved under transition metal-free reaction condition. Various aryl ketone derivatives react readily with DMSO, producing the α,β-unsaturated carbonyl compounds in yields of 42 to 90%. This method features a transition metal-free reaction condition, wide substrate scope and using DMSO as novel one-carbon source to form C═C bond, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyl compounds. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00619

DOI: 10.1021/acs.joc.7b00619

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.