Decarboxylative Alkynylation

Joel M. Smith, Tian Qin, Rohan R. Merchant, Jacob T. Edwards, Lara R. Malins, Zhiqing Liu, Guanda Che, Zichao Shen, Scott A. Shaw, Martin D. Eastgate, Phil S. Baran

Research output: Contribution to journalArticle

64 Scopus citations

Abstract

The development of a new decarboxylative cross-coupling method that affords terminal and substituted alkynes from various carboxylic acids is described using both nickel- and iron-based catalysts. The use of N-hydroxytetrachlorophthalimide (TCNHPI) esters is crucial to the success of the transformation, and the reaction is amenable to in situ carboxylic acid activation. Additionally, an inexpensive, commercially available alkyne source is employed in this formal homologation process that serves as a surrogate for other well-established alkyne syntheses. The reaction is operationally simple and broad in scope while providing succinct and scalable avenues to previously reported synthetic intermediates.

Original languageEnglish (US)
Pages (from-to)11906-11910
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number39
DOIs
Publication statusPublished - Jan 1 2017
Externally publishedYes

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Keywords

  • alkynylation
  • homologation
  • iron catalysis
  • nickel catalysis
  • redox-active esters

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Smith, J. M., Qin, T., Merchant, R. R., Edwards, J. T., Malins, L. R., Liu, Z., ... Baran, P. S. (2017). Decarboxylative Alkynylation. Angewandte Chemie - International Edition, 56(39), 11906-11910. https://doi.org/10.1002/anie.201705107