Synthesis 2023; 55(19): 3186-3194
DOI: 10.1055/a-2114-7802
paper

Transition-Metal-Free and Selective Deconstructive Carbonyl Olefination of α-Hydroxy Ketones: A Complementary Approach to Knoevenagel Reaction

Sandeep Sandeep
a   Department of Applied Sciences, University Institute of Engineering and Technology, Panjab University, Chandigarh 160014, India
b   Department of Chemistry, Panjab University, Chandigarh 160014, India
,
b   Department of Chemistry, Panjab University, Chandigarh 160014, India
,
Chayawan Chayawan
c   Department of Chemistry, National Institute of Technology, Hamirpur, Himachal Pradesh 177005, India
,
Ganga R. Chaudhary
b   Department of Chemistry, Panjab University, Chandigarh 160014, India
,
Paloth Venugopalan
b   Department of Chemistry, Panjab University, Chandigarh 160014, India
,
Anil Kumar
a   Department of Applied Sciences, University Institute of Engineering and Technology, Panjab University, Chandigarh 160014, India
› Author Affiliations
A.K. is grateful to the Science and Engineering Research Board, India, for the SERB-TARE project (Grant Number TAR/2022/000045).


Abstract

While the carbonyl olefination has been extensively studied and well documented, use of α-hydroxy ketones as precursors for the carbonyl olefination is not reported, till date. Herein, a transition-metal-free and selective Knoevenagel-type deconstructive carbonyl olefination of α-hydroxy ketones using arylacetonitriles under mild reaction conditions is presented. The reaction affords valuable scaffolds of acrylonitriles with the use of α-hydroxy ketones as precursors for carbonyl olefination.

Supporting Information



Publication History

Received: 21 May 2023

Accepted after revision: 21 June 2023

Accepted Manuscript online:
21 June 2023

Article published online:
17 July 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany