Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis

Hsin Chun Chiu, Ian A. Tonks

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

Trimethylsilyl (TMS)-protected alkynes served as selective alkyne cross-coupling partners in titanium-catalyzed [2+2+1] pyrrole synthesis. Reactions of TMS-protected alkynes with internal alkynes and azobenzene under the catalysis of titanium imido complexes yielded pentasubstituted 2-TMS-pyrroles with greater than 90 % selectivity over the other nine possible pyrrole products. The steric and electronic effects of the TMS group were both identified to play key roles in this highly selective pyrrole synthesis. This strategy provides a convenient method to synthesize multisubstituted pyrroles as well as an entry point for further pyrrole diversification through facile modification of the resulting 2-silyl pyrrole products, as demonstrated through a short formal synthesis of the marine natural product lamellarin R.

Original languageEnglish (US)
Pages (from-to)6090-6094
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number21
DOIs
StatePublished - May 22 2018

Bibliographical note

Funding Information:
Financial support was provided by the National Institutes of Health (1R35GM119457). The Chemistry Department NMR facility is supported through a grant from the National Institutes of Health (S10OD011952) with matching funds from the University of Minnesota. IAT is a 2017 Alfred P. Sloan Fellow.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • alkynes
  • cycloaddition
  • multicomponent reactions
  • pyrroles
  • titanium

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