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Selective Homogeneous and Heterogeneous Gold Catalysis with Alkynes and Alkenes: Similar Behavior, Different Origin
Author(s) -
GarcíaMota Mónica,
Cabello Noemí,
Maseras Feliu,
Echavarren Antonio M.,
PérezRamírez Javier,
Lopez Nuria
Publication year - 2008
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.200800246
Subject(s) - catalysis , homogeneous , heterogeneous catalysis , homogeneous catalysis , chemistry , selectivity , colloidal gold , combinatorial chemistry , electrophile , enyne , nanotechnology , computational chemistry , nanoparticle , organic chemistry , materials science , thermodynamics , physics
The development of new sustainable chemical processes requires the implementation of ultra‐selective reaction processes. The enormous selectivity found for gold‐based catalysts when applied in several reactions has opened new frontiers. For instance, the selective activation of alkynes is a common feature for both homogeneous and heterogeneous gold catalysts. Herein, we employ experimental and theoretical methods to assess the similarities and differences in the performance of homogeneous and heterogeneous gold catalysts. Alkynophilicity, the selective activation of alkynes, is found to have a thermodynamic origin in the heterogeneous case and a kinetic one for homogeneous catalysis. Complex enyne rearrangements require the more active homogeneous (single gold) catalyst because it has more electrophilic character than its heterogeneous (nanoparticle) counterpart.