Full Paper

Synthesis of Fluorenes via the Palladium-Catalyzed 5-exo-dig Annulation of o-Alkynylbiaryls

  1. Natalia Chernyak,
  2. Vladimir Gevorgyan

Article first published online: 5 MAY 2009

DOI: 10.1002/adsc.200800765

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 351, Issue 7-8, pages 1101–1114, May 2009

Additional Information

How to Cite

Chernyak, N. and Gevorgyan, V. (2009), Synthesis of Fluorenes via the Palladium-Catalyzed 5-exo-dig Annulation of o-Alkynylbiaryls. Adv. Synth. Catal., 351: 1101–1114. doi: 10.1002/adsc.200800765

Author Information

  1. Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA, Fax: (+1)-312-355-0836; phone: (+1)-312-355-3579

Publication History

  1. Issue published online: 12 MAY 2009
  2. Article first published online: 5 MAY 2009
  3. Manuscript Revised: 4 FEB 2009
  4. Manuscript Received: 10 DEC 2008

Funded by

  • National Institutes of Health. Grant Number: GM-64444
  • National Science Foundation. Grant Number: CHE-0710749

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Keywords:

  • alkynes;
  • annulations;
  • arylation;
  • C[BOND]H activation;
  • palladium

Abstract

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The direct palladium-catalyzed intramolecular hydroarylation of o-alkynylbiaryls proceeded in a highly stereoselective manner producing fluorenes 2, the products of 5-exo-dig cyclization, in excellent yields. The cascade intermolecular arylation, incorporated in this transformation, allowed for the efficient synthesis of fully substituted fluorenes 12. These cyclizations proceed more rapidly with electron-deficient benzene rings which, in combination with a substantial isotope effect observed, strongly supports a C[BOND]H activation mechanism for the key annulation step.

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