Synthesis of Fluorenes  via  the Palladium‐Catalyzed 5‐ exo‐dig  Annulation of  o ‐Alkynylbiaryls | Zendy

Chernyak Natalia | Zendy; Gevorgyan Vladimir | Zendy

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

Author(s) -

Chernyak Natalia,

Gevorgyan Vladimir

Publication year - 2009

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.200800765

Subject(s) - chemistry , annulation , intramolecular force , palladium , catalysis , dig , intermolecular force , benzene , cascade , stereochemistry , stereoselectivity , medicinal chemistry , combinatorial chemistry , molecule , organic chemistry , computer security , computer science , chromatography

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 CH activation mechanism for the key annulation step.

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