Issue 81, 2017

The acid promoted Petasis reaction of organotrifluoroborates with imines and enamines

Abstract

The acid promoted addition of organotrifluoroborate salts to imine and enamine electrophiles is reported. Use of the pre-activated trifluoroboronate complex bypasses the need for α-hetero substitution on the electrophile component, greatly expanding the scope of the Petasis borono–Mannich reaction. A variety of vinyl, aromatic and heteroaromatic trifluoroborate salts undergo addition with good efficiency under mild reaction conditions. The reaction is amenable for use with a variety of carbamate protected imine and enamine electrophiles, achieving for the first time the effective coupling with aliphatic aldehydes.

Graphical abstract: The acid promoted Petasis reaction of organotrifluoroborates with imines and enamines

Supplementary files

Article information

Article type
Communication
Submitted
06 Jun 2017
Accepted
14 Sep 2017
First published
15 Sep 2017

Chem. Commun., 2017,53, 11185-11188

The acid promoted Petasis reaction of organotrifluoroborates with imines and enamines

D. E. Carrera, Chem. Commun., 2017, 53, 11185 DOI: 10.1039/C7CC04397J

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