Mechanistic Insight into the Catalytic Staudinger Ligation

Paul B White, Sjoerd J Rijpkema, Roderick P Bunschoten, Jasmin Mecinović

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

Organophosphorus-catalyzed Staudinger ligation between carboxylic acids and azides in the presence of phenylsilane reductant produces amides. NMR-based mechanistic investigations revealed that the catalytic Staudinger ligation does not proceed via reduction of phosphine oxide but rather via reduction of iminophosphorane, which can subsequently undergo several transformations to produce the amide product.

Original languageEnglish
JournalOrganic Letters
Volume21
Issue number4
Pages (from-to)1011-1014
ISSN1523-7060
DOIs
Publication statusPublished - 15. Feb 2019

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