Fluorinated acrylates via alkoxycarbonylation of 1-alkynes with fluorinated alcohols

The system formed by combining in situ Pd(OAc)2 with (2-pyridyl)diphenylphosphine (PyPPh2) and CH3SO3H catalyzes efficiently the carbonylation of terminal alkynes (phenylacetylene or 1-hexyne) with alcohols having perfluorinated segments of the type CF3(CF2)m(CH2)n–OH (m=1 or 3, n=1, 2 or 3) or with...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2014-09, Vol.70 (35), p.5434-5438
Main Authors: Scrivanti, Alberto, Bertoldini, Matteo, Aversa, Manuela, Beghetto, Valentina, Zancanaro, Aurora, Paganelli, Stefano, Matteoli, Ugo
Format: Article
Language:English
Subjects:
Acrylates
Alcohols
Alkynes
Carbonylation
Carbonyls
Esters
Fluorinated acrylates
Fluorinated alcohols
Fluorination
Palladium
Segments
Terminals
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The system formed by combining in situ Pd(OAc)2 with (2-pyridyl)diphenylphosphine (PyPPh2) and CH3SO3H catalyzes efficiently the carbonylation of terminal alkynes (phenylacetylene or 1-hexyne) with alcohols having perfluorinated segments of the type CF3(CF2)m(CH2)n–OH (m=1 or 3, n=1, 2 or 3) or with pentafluorophenol. Good carbonylation rates accompanied by high regioselectivity towards acrylate ester formation are obtained under mild reaction conditions (T=60–80 °C, P(CO)=30 atm). The influence of the CO pressure, the catalyst composition, the temperature and the number (n) of protonated methylene groups on the catalysis has been studied. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.06.123