Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems

Natalia Chernyak; David Tilly; Zhou Li; Vladimir Gevorgyan

doi:10.1039/b919991h

Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems

Natalia Chernyak, David Tilly, Zhou Li, Vladimir Gevorgyan

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

56 Scopus citations

Abstract

Polycyclic indole structures, possessing fused seven-membered rings were efficiently synthesized via the Pd-catalyzed intramolecular carbopalladation- annulation of 3-(2-iodobenzyl)-indoles and alkynes. A remarkable base effect on the chemoselectivity of this transformation has been found: switching from Et₃N to CsOAc completely reverses the reaction path to intramolecular cyclization forming fused five-membered rings.

Original language	English (US)
Pages (from-to)	150-152
Number of pages	3
Journal	Chemical Communications
Volume	46
Issue number	1
DOIs	https://doi.org/10.1039/b919991h
State	Published - 2010
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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abstract = "Polycyclic indole structures, possessing fused seven-membered rings were efficiently synthesized via the Pd-catalyzed intramolecular carbopalladation- annulation of 3-(2-iodobenzyl)-indoles and alkynes. A remarkable base effect on the chemoselectivity of this transformation has been found: switching from Et3N to CsOAc completely reverses the reaction path to intramolecular cyclization forming fused five-membered rings.",

author = "Natalia Chernyak and David Tilly and Zhou Li and Vladimir Gevorgyan",

year = "2010",

doi = "10.1039/b919991h",

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AU - Chernyak, Natalia

AU - Tilly, David

AU - Li, Zhou

AU - Gevorgyan, Vladimir

PY - 2010

Y1 - 2010

N2 - Polycyclic indole structures, possessing fused seven-membered rings were efficiently synthesized via the Pd-catalyzed intramolecular carbopalladation- annulation of 3-(2-iodobenzyl)-indoles and alkynes. A remarkable base effect on the chemoselectivity of this transformation has been found: switching from Et3N to CsOAc completely reverses the reaction path to intramolecular cyclization forming fused five-membered rings.

AB - Polycyclic indole structures, possessing fused seven-membered rings were efficiently synthesized via the Pd-catalyzed intramolecular carbopalladation- annulation of 3-(2-iodobenzyl)-indoles and alkynes. A remarkable base effect on the chemoselectivity of this transformation has been found: switching from Et3N to CsOAc completely reverses the reaction path to intramolecular cyclization forming fused five-membered rings.

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Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems

Abstract

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