Fluoride-Promoted Rearrangement of Organo Silicon Compounds: A New Synthesis of 2-(Arylmethyl)aldehydes from 1-Alkynes
Laura Antonella Aronica, Patrizio Raffa, Anna Maria Caporusso and Piero Salvadori*
*Dipartimento di Chimica e Chimica Industriale, Università degli Studi di
Pisa, Via Risorgimento 35, 56126 Pisa, Italy, Email: psalva
dcci.unipi.it
L. A. Aronica, P. Raffa, A. M. Caporusso, P. Salvadori, J. Org. Chem., 2003, 5, 9292-9298.
DOI: 10.1021/jo0351062
Abstract
A new approach to 2-(arylmethyl)aldehydes begins with a silylformylation reaction of terminal acetylenes with aryl- or heteroarylsilanes, followed by treatment of the products with TBAF to induce a 1,2-anionotropic rearrangement of the aryl group.
see article for more examples
proposed
mechanism
Key Words
2-Arylmethylaldehydes, Arenes, Vinylsilanes, Carbonylation, Rearrangement
ID: J42-Y2003-1070
