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

61 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
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/b919991h

Cite this

@article{ca214fc92ef64621b17adfe637c1074b,

title = "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 = "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",

language = "English (US)",

volume = "46",

pages = "150--152",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "1",

}

TY - JOUR

T1 - Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems

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.

UR - http://www.scopus.com/inward/record.url?scp=72149087732&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=72149087732&partnerID=8YFLogxK

U2 - 10.1039/b919991h

DO - 10.1039/b919991h

M3 - Article

C2 - 20024323

AN - SCOPUS:72149087732

SN - 1359-7345

VL - 46

SP - 150

EP - 152

JO - Chemical Communications

JF - Chemical Communications

IS - 1

ER -

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

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this