Highly diastereoselective Heck-Matsuda reaction with pyrazolyl diazonium salts

The Heck-Matsuda (HM) reaction is a powerful synthetic approach cut out for C-C bonds formation under mild conditions. We demonstrated that pyrazolyl diazonium salts are suitable reagents in this protocol, allowing us to deliver highly substituted cyclopentenols and cyclopentenamines with an excelle...

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Bibliographic Details
Published in:New journal of chemistry 2023-05, Vol.47 (21), p.9994-9997
Main Authors: Bellina, F, Berti, F, Bertozzi, S. M, Bandiera, T, Bertozzi, F
Format: Article
Language:English
Subjects:
Covalent bonds
Enantiomers
Reagents
Stereoselectivity
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Summary:The Heck-Matsuda (HM) reaction is a powerful synthetic approach cut out for C-C bonds formation under mild conditions. We demonstrated that pyrazolyl diazonium salts are suitable reagents in this protocol, allowing us to deliver highly substituted cyclopentenols and cyclopentenamines with an excellent degree of diastereoselectivity and a control of enantioselectivity. Novel pyrazolyl-derived diazonium tetrafluoroborate salts were used in the palladium-catalyzed Heck-Matsuda reaction for the diastereoselective synthesis of highly substituted cyclopenten-ols/-amines.
ISSN:1144-0546
1369-9261
DOI:10.1039/d3nj01724a