Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 33, Pages 11598-11601Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja5059795
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Funding
- National Research Foundation Singapore [NRF-RF-2009-05]
- Nanyang Technological University
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A palladium(II) catalyst promotes condensation of an N-aryl imine and an alkynylbenziodoxolone derivative to afford a multisubstituted furan, whose substituents are derived from the alkynyl moiety (2-position), the imine (3- and 4-positions), and the 2-iodobenzoate moiety (5-position), along with an N-arylformamide under mild conditions. The 2-iodophenyl group of the furan product serves as a versatile handle for further transformations. A series of isotope-labeling experiments shed light on the bond reorganization process in this unusual condensation reaction, which includes cleavage of the C C triple bond and fragmentation of the carboxylate moiety.
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