Journal
ORGANOMETALLICS
Volume 30, Issue 22, Pages 6328-6337Publisher
AMER CHEMICAL SOC
DOI: 10.1021/om2009556
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Funding
- ERC
- EPSRC
- Spanish MICINN [RYC-2009-04170]
- Royal Society
- EPSRC [EP/H015418/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/H015418/1] Funding Source: researchfish
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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 pi activation of the alkyne framework of the carboxamides, and the second represents an unusual use of the basic Bronsted character of [Au(IPr)(OH)). Mechanistic and DFT studies support the mechanistic hypotheses.
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