Journal
ORGANIC LETTERS
Volume 12, Issue 23, Pages 5538-5541Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol1024794
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Funding
- Natural Science Foundation of China [20872105, 21002073]
- National Institutes of Health of the U.S. [GM-64444]
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A mechanism of the Au-catalyzed cycloisomerization of propargylpyridines has been investigated. Both DFT computational and experimental results strongly support generation of a Au-carbene via a cyclization/proton transfer sequence over the previously proposed path involving a Au-vinylidene intermediate. For the beta-Si-substituted Au-carbene (G = SiR3), a 1,2-Si migration was shown to be kinetically favored over a 1,2-H shift. This study highlights the importance of alternative pathways that could explain reactivities commonly attributed to an alkyne-vinylidene isomerization in Au catalysis.
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