Palladium-catalyzed carbocyclization of alkynyl ketones proceeding through a carbopalladation pathway

Natalia Chernyak; Serge I. Gorelsky; Vladimir Gevorgyan

doi:10.1002/anie.201006751

Palladium-catalyzed carbocyclization of alkynyl ketones proceeding through a carbopalladation pathway

Natalia Chernyak, Serge I. Gorelsky, Vladimir Gevorgyan

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

80 Scopus citations

Abstract

Dig this: 5-exo-dig carbocyclization of 1 into 2 features intramolecular carbopalladation of alkyne with Pd enolate (see scheme). DFT calculations show that the key Pd enolate forms by deprotonation assisted byb Pd^II acetate. Subsequent intramolecular alkyne carbopalladation, Z-E isomerization of the formed vinyl palladium species, and protiodepalladation leads to E-alkylidene indanones. (Chemical Equation Presented).

Original language	English (US)
Pages (from-to)	2342-2345
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	10
DOIs	https://doi.org/10.1002/anie.201006751
State	Published - Mar 1 2011
Externally published	Yes

Keywords

C-H activation
Carbocyclization
Computational chemistry
Homogeneous catalysis
Palladium

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201006751

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title = "Palladium-catalyzed carbocyclization of alkynyl ketones proceeding through a carbopalladation pathway",

abstract = "Dig this: 5-exo-dig carbocyclization of 1 into 2 features intramolecular carbopalladation of alkyne with Pd enolate (see scheme). DFT calculations show that the key Pd enolate forms by deprotonation assisted byb PdII acetate. Subsequent intramolecular alkyne carbopalladation, Z-E isomerization of the formed vinyl palladium species, and protiodepalladation leads to E-alkylidene indanones. (Chemical Equation Presented).",

keywords = "C-H activation, Carbocyclization, Computational chemistry, Homogeneous catalysis, Palladium",

author = "Natalia Chernyak and Gorelsky, {Serge I.} and Vladimir Gevorgyan",

year = "2011",

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doi = "10.1002/anie.201006751",

language = "English (US)",

volume = "50",

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T1 - Palladium-catalyzed carbocyclization of alkynyl ketones proceeding through a carbopalladation pathway

AU - Chernyak, Natalia

AU - Gorelsky, Serge I.

AU - Gevorgyan, Vladimir

PY - 2011/3/1

Y1 - 2011/3/1

N2 - Dig this: 5-exo-dig carbocyclization of 1 into 2 features intramolecular carbopalladation of alkyne with Pd enolate (see scheme). DFT calculations show that the key Pd enolate forms by deprotonation assisted byb PdII acetate. Subsequent intramolecular alkyne carbopalladation, Z-E isomerization of the formed vinyl palladium species, and protiodepalladation leads to E-alkylidene indanones. (Chemical Equation Presented).

AB - Dig this: 5-exo-dig carbocyclization of 1 into 2 features intramolecular carbopalladation of alkyne with Pd enolate (see scheme). DFT calculations show that the key Pd enolate forms by deprotonation assisted byb PdII acetate. Subsequent intramolecular alkyne carbopalladation, Z-E isomerization of the formed vinyl palladium species, and protiodepalladation leads to E-alkylidene indanones. (Chemical Equation Presented).

KW - C-H activation

KW - Carbocyclization

KW - Computational chemistry

KW - Homogeneous catalysis

KW - Palladium

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DO - 10.1002/anie.201006751

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SN - 1433-7851

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SP - 2342

EP - 2345

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 10

ER -

Palladium-catalyzed carbocyclization of alkynyl ketones proceeding through a carbopalladation pathway

Abstract

Keywords

ASJC Scopus subject areas

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