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- Title
"On water" Catalytic Michael Addition Between α,β-Unsaturated Ketone and Nitromethane.
- Authors
Wang, Yuping; Han, Jinsong; Liu, Yu; Zhang, Panpan; Wei, Wanyao; Jian, Yajun
- Abstract
The first systematic "on water" Michael addition between α,β-unsaturated ketone and nitromethane has been developed, credited to the introduction of an extra hydrogen bond forming site, N-methyl imidazole group, which is adjacent to the carbonyl group of ketones with their electrophilic activity enhanced. Moreover, a reaction rate enhancement was observed on water than in other organic solvents. In addition, the solvent deuterium isotope effect test and contact angle measurement indicate that N-methyl imidazole bearing substrates are prone to form hydrogen bonds with water. Our results not only expand the reaction scope of on water catalysis, but also provide insight for selecting suitable substrates for on water reactions.
- Subjects
KETONES; NITROMETHANE; HYDROGEN bonding; CONTACT angle; CARBONYL group; IMIDAZOLES
- Publication
Catalysis Letters, 2022, Vol 152, Issue 11, p3338
- ISSN
1011-372X
- Publication type
Article
- DOI
10.1007/s10562-021-03904-1