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

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JournalACS Catalysis
DateAccepted/In press - 4 Dec 2018
DateE-pub ahead of print - 4 Dec 2018
DatePublished (current) - 4 Jan 2019
Issue number1
Volume9
Number of pages7
Pages (from-to)504-510
Early online date4/12/18
Original languageEnglish

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

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© 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.

    Research areas

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

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