Abstract
The direct palladium-catalyzed intramolecular hydro arylation 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-H activation mechanism for the key annulation step.
Original language | English (US) |
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Pages (from-to) | 1101-1114 |
Number of pages | 14 |
Journal | Advanced Synthesis and Catalysis |
Volume | 351 |
Issue number | 7-8 |
DOIs | |
State | Published - May 2009 |
Externally published | Yes |
Keywords
- Alkynes
- Annulations
- Arylation
- C-H activation
- Palladium
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry