Petasis reaction
Abstract
The Petasis reaction is a three-component reaction that couples an aldehyde (or ketone), an amine, and a boronic acid to produce a substituted amine.
Keywords
Multicomponent reaction, Amine, Aldehyde, Ketone, Boronic acid
Category
Multicomponent reaction
Mechanism
First, the nucleophilic addition of the amine on the carbonyl carbon forms a hemiaminal intermediate. After a prototropy, the hydroxyl group then coordinates the boron of the boronic acid. The organic group on the boronic acid subsequently migrates from boron to the α-carbon relative to the amino group, forming a new C-C bond and releasing boric acid (B(OH)3) as by-product.
Recent review
Saeed, S.; Munawar, S.; Ahmad, S.; Mansha, A.; Zahoor, A.F.; Irfan, A.; Irfan, A.; Kotwica-Mojzych, K.; Soroka, M.; Głowacka, M.; Mojzych, M. Recent Trends in the Petasis Reaction: A Review of Novel Catalytic Synthetic Approaches with Applications of the Petasis Reaction. Molecules. 2023, 28, 8032-8051.