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Publication Details
AFRICAN RESEARCH NEXUS
SHINING A SPOTLIGHT ON AFRICAN RESEARCH
chemistry
Selectivity switch in the synthesis of vinylgold(I) intermediates
Organometallics, Volume 30, No. 22, Year 2011
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Description
An unexpected regioselectivity reversal was observed in the synthesis of vinylgold(I) complexes from propargyl carboxamides. The use of [Au(IPr)(OH)] affords preferentially vinylgold(I) complexes resulting from a 5-exo-dig cyclization, whereas the use [Au(IPr)]+ species, generated in situ starting from [Au(IPr)(Cl)] and AgOTf, leads to vinylgold(I) complexes which form via a 6-endo-dig cyclization, This unexpected "selectivity switch" for this cyclization led us to propose two different reaction pathways enabling the formation of the two different products. One mechanism involves the [Au(IPr)]+ species with "classical" I activation of the alkyne framework of the carboxamides, and the second represents an "unusual" use of the basic Brønsted character of [Au(IPr)(OH)]. Mechanistic and DFT studies support the mechanistic hypotheses. © 2011 American Chemical Society.
Authors & Co-Authors
Hashmi, A. Stephen K.
Germany, Heidelberg
Universität Heidelberg
Schuster, Andreas M.
Germany, Heidelberg
Universität Heidelberg
Gaillard, Sylvain
United Kingdom, St Andrews
University of st Andrews
France, Caen
Université de Caen Normandie
Cavallo, Luigi
Italy, Salerno
Università Degli Studi Di Salerno
Saudi Arabia, Thuwal
King Abdullah University of Science and Technology
Poater, Albert
Spain, Girona
Universitat de Girona
Nolan, Steven Patrick
United Kingdom, St Andrews
University of st Andrews
Statistics
Citations: 101
Authors: 6
Affiliations: 6
Identifiers
Doi:
10.1021/om2009556
ISSN:
02767333
e-ISSN:
15206041