Golden Carousel in Catalysis: The Cationic Gold/Propargylic Ester Cycle

Round and round it goes: Propargylic esters are versatile substrates for Au‐based catalysts. However, under typical conditions the starting Au‐coordinated propargylic ester 1 is in rapid equilibrium with the gold vinylic carbenoid species 2 and with gold allene species 3. A number of factors dictate...

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Published inAngewandte Chemie (International ed.) Vol. 47; no. 4; pp. 718 - 721
Main Authors Correa, Andrea, Marion, Nicolas, Fensterbank, Louis, Malacria, Max, Nolan, Steven P, Cavallo, Luigi
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2008
WILEY-VCH Verlag
WILEY‐VCH Verlag
Subjects
alkynes
Alkynes - chemistry
allenes
Catalysis
Cations - chemistry
density functional calculations
Esters - chemistry
gold
Gold - chemistry
homogeneous catalysis
Ligands
Models, Chemical
Molecular Structure
Stereoisomerism
Thermodynamics
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Summary:Round and round it goes: Propargylic esters are versatile substrates for Au‐based catalysts. However, under typical conditions the starting Au‐coordinated propargylic ester 1 is in rapid equilibrium with the gold vinylic carbenoid species 2 and with gold allene species 3. A number of factors dictate which intermediate is lower in energy and which type of products form.
Bibliography:http://dx.doi.org/10.1002/anie.200703769
Ministerio de Educación y Ciencia
ICREA
istex:18C7A06359ECF47116AC3268337F825E6708CEB6
ANR
Petroleum Research Fund
ark:/67375/WNG-F59KV3TH-C
ArticleID:ANIE200703769
L.C. thanks the Regione Campania (Progetto Legge 5, 2006) for financial support, and CINECA (INSTM grant) for computer time. S.P.N. acknowledges the Petroleum Research Fund administered by the ACS, the Ministerio de Educación y Ciencia, the ICIQ Foundation and ICREA for partial funding. S.P.N. is an ICREA Research Professor. N.M. thanks the AGAUR for a pre-doctoral fellowship (2007 FI_A 01466). L.F. and M.M. thank the ANR "allènes" BLAN 06-2_159258.
ICIQ Foundation
Regione Campania
L.C. thanks the Regione Campania (Progetto Legge 5, 2006) for financial support, and CINECA (INSTM grant) for computer time. S.P.N. acknowledges the Petroleum Research Fund administered by the ACS, the Ministerio de Educación y Ciencia, the ICIQ Foundation and ICREA for partial funding. S.P.N. is an ICREA Research Professor. N.M. thanks the AGAUR for a pre‐doctoral fellowship (2007 FI_A 01466). L.F. and M.M. thank the ANR “allènes” BLAN 06‐2_159258.
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200703769