Journal
ACS CATALYSIS
Volume 11, Issue 1, Pages 199-207Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c04217
Keywords
acrylate; aryloxide; BHT; chemoselectivity; DFT calculations; magnesium; sodium; transesterification
Categories
Funding
- JSPS KAKENHI [JP20H02735, JP15H05755, JP15H05810, JP15H05805]
- Shorai Foundation for Science and Technology
- Integrated Research Consortium on Chemical Sciences
Ask authors/readers for more resources
A highly chemoselective transesterification catalyzed by NaOAr or Mg(OAr)2 was developed, allowing for the production of functionalized acrylates without undesired Michael additions under mild reaction conditions. Computational density functional theory calculations supported the high chemoselectivity of this reaction.
A highly chemoselective transesterification of methyl (meth)acrylates catalyzed by sterically demanding 2,6-di-tert-butyl-4-methylphenol-derived NaOAr or Mg(OAr)(2) was developed. The desired transesterification proceeded without the undesired Michael additions under mild reaction conditions at 25 degrees C, and various primary and secondary alcohols, diols, triol, and tetraol on a scale of up to 10 mmol could provide the corresponding functionalized acrylates in high yields. Transition states were proposed based on monomeric and dimeric active species, and computational density functional theory calculations strongly supported high chemoselectivity to minimize undesired Michael additions.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available