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)neOH (m¼1 or 3, n¼1, 2 or 3) or with pentafluorophenol. Good carbonylation rates accompanied by high regioselectivity towards acrylate ester formation are obtained under mild reaction conditions (T¼60e80 C, P(CO)¼30 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.

Fluorinated acrylates via alkoxycarbonylation of 1-alkynes with fluorinated alcohols

SCRIVANTI, Alberto;BERTOLDINI, Matteo;AVERSA, MANUELA;BEGHETTO, Valentina;PAGANELLI, Stefano;MATTEOLI, Ugo
2014-01-01

Abstract

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)neOH (m¼1 or 3, n¼1, 2 or 3) or with pentafluorophenol. Good carbonylation rates accompanied by high regioselectivity towards acrylate ester formation are obtained under mild reaction conditions (T¼60e80 C, P(CO)¼30 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.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10278/42417
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