Merging π-Acid and Pd Catalysis: Dearomatizing Spirocyclization/Cross-Coupling Cascade Reactions of Alkyne-Tethered Aromatics

Hon Eong Ho, Thomas Christian Stephens, Thomas Payne, Peter Andrew O'Brien, Richard John Kenneth Taylor, William Paul Unsworth

Research output: Contribution to journal › Article › peer-review

Abstract

A one-pot protocol for the dearomatising spirocyclisation/cross coupling of alkyne-tethered indoles/pyrroles is described. Mechanistic studies support a process by which palladium complexes generated in situ act as both π-acid and cross coupling catalysts. Overall, this facilitates an efficient cascade process that enables the simultaneous preparation of synthetically challenging quaternary spirocyclic carbons and tetrasubstituted alkenes in a single operation. KEYWORDS spirocycles, dearomatisation, cross coupling, palladium, catalysis
Original languageEnglish
Pages (from-to)504-510
Number of pages7
JournalACS Catalysis
Volume9
Issue number1
Early online date4 Dec 2018
DOIs
Publication statusPublished - 4 Jan 2019

Bibliographical note

© 2018 American Chemical Society. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

Keywords

  • catalysis
  • cross-coupling
  • dearomatization
  • palladium
  • spirocycles

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  • Ho Pd spiro ACS template version 8 revision

    © 2018 American Chemical Society. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

    Accepted author manuscript, 590 KB

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