期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 4, 期 8, 页码 1230-1236出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200900091
关键词
allenoates; cyclizations; gold; organogold complexes; reaction mechanisms
资金
- National Science Foundation [CHE-0809683]
The reaction of allenoates with cationic gold (I)-generated in situ from a phosphine gold chloride and a silver salt-formed unusual, room temperature stable vinyl gold(I) lactones under very mild conditions. The scope and limitations for the synthesis of this novel organogold complex was investigated. DFT calculations oil the highest occupied molecular orbitals (HOMOs) of allenoates and the natural bond orbital (NBO) charge densities provided an explanation for the limitations. A plausible mechanism for its formation was proposed based on in situ H-1 and P-31 NMR spectroscopic analyses. Controlled experiments for the cleavage of the gold-carbon bond by electrophiles indicated that this vinyl gold(I) complex is the likely intermediate in the gold-catalyzed reaction of carboncarbon multiple bonds.
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