Unexpected reactivity of pyridinium salts toward alkynyl Fischer complexes to produce oxo‐heterocycles

The unprecedented reaction of ketone‐containing aromatic pyridinium salts 3a‐e and alkynyl Fischer complexes 1a‐f proceeds via a mild domino process to provide 4,6‐disubstituted pyran‐2‐ones 5a‐k and 2,3,5‐trisubstituted furans 6a‐h (45‐97%). According of the results of isotopic labeling experiments...

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Published inApplied organometallic chemistry Vol. 32; no. 3
Main Authors Flores‐Conde, María Inés, Cruz, Fabiola N., López, Julio, Jiménez‐Halla, J. Óscar C., Peña‐Cabrera, Eduardo, Flores‐Álamo, Marcos, Delgado, Francisco, Vázquez, Miguel A.
Format Journal Article
LanguageEnglish
Published Chichester Wiley Subscription Services, Inc 01.03.2018
Subjects
Alkynyl Fischer carbene
Chemistry
disubstituted 2H‐pyran‐2‐one
Furans
Isotopic labeling
pyridine ylide
trisubstituted furan
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Summary:The unprecedented reaction of ketone‐containing aromatic pyridinium salts 3a‐e and alkynyl Fischer complexes 1a‐f proceeds via a mild domino process to provide 4,6‐disubstituted pyran‐2‐ones 5a‐k and 2,3,5‐trisubstituted furans 6a‐h (45‐97%). According of the results of isotopic labeling experiments, a mechanism involving an initial Michael addition appears to be the key step, obtaining a mesomeric structure responsible for the formation of both products. An unexpected reactivity of alkynyl Fischer carbenes and pyridinium salts were found. A plausible mechanism for the formation of the oxo‐heterocycles involves a domino process. Through this method, pyran‐2‐ones are obtained in a selective fashion.
ISSN:0268-2605
1099-0739
DOI:10.1002/aoc.4202