Abstract
AbstractA new approach for the synthesis of coumarins from siloxy alkynes and salicylaldehydes is disclosed. Unlike the previous benzannulation reactions of siloxy alkynes that all proceed by electron-inversed Diels–Alder mechanism, this process represents a new [4+2] cyclization. In the presence of the superior HNTf2 catalyst, a wide range of coumarins were efficiently synthesized. This process was also extended to the synthesis of 2-quinolones. The polarized electron-rich triple bond might react sequentially with the aldehyde and hydroxy group by polarity switching in the stepwise formation of the C–C and C–O bonds. Control experiments provided insights into the mechanistic understanding.
Funder
Science, Technology and Innovation Commission of Shenzhen Municipality
Research Grants Council, University Grants Committee
Cited by
4 articles.
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