Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles

Kalicharan Chattopadhyay; Erik Fenster; Alexander J. Grenning; Jon A. Tunge

doi:10.3762/bjoc.8.133

Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles

Kalicharan Chattopadhyay, Erik Fenster, Alexander J. Grenning, Jon A. Tunge

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

4 Scopus citations

Abstract

The palladium-catalyzed nucleophilic substitution of (coumarinyl)methyl acetates is described. The reaction proceeds though a palladium ?-benzyl-like complex and allows for many different types of C-, N-, and S-nucleophiles to be regioselectively added to the biologically active coumarin motif. This new method was utilized to prepare a 128-membered library of aminated coumarins for biological screening.

Original language	English (US)
Pages (from-to)	1200-1207
Number of pages	8
Journal	Beilstein Journal of Organic Chemistry
Volume	8
DOIs	https://doi.org/10.3762/bjoc.8.133
State	Published - Jul 27 2012
Externally published	Yes

Keywords

Benzylation
Catalysis
Chemical diversity
Coumarin
Decarboxylative
Palladium
Substitution

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10.3762/bjoc.8.133

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abstract = "The palladium-catalyzed nucleophilic substitution of (coumarinyl)methyl acetates is described. The reaction proceeds though a palladium ?-benzyl-like complex and allows for many different types of C-, N-, and S-nucleophiles to be regioselectively added to the biologically active coumarin motif. This new method was utilized to prepare a 128-membered library of aminated coumarins for biological screening.",

keywords = "Benzylation, Catalysis, Chemical diversity, Coumarin, Decarboxylative, Palladium, Substitution",

author = "Kalicharan Chattopadhyay and Erik Fenster and Grenning, {Alexander J.} and Tunge, {Jon A.}",

year = "2012",

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language = "English (US)",

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T1 - Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles

AU - Chattopadhyay, Kalicharan

AU - Fenster, Erik

AU - Grenning, Alexander J.

AU - Tunge, Jon A.

PY - 2012/7/27

Y1 - 2012/7/27

N2 - The palladium-catalyzed nucleophilic substitution of (coumarinyl)methyl acetates is described. The reaction proceeds though a palladium ?-benzyl-like complex and allows for many different types of C-, N-, and S-nucleophiles to be regioselectively added to the biologically active coumarin motif. This new method was utilized to prepare a 128-membered library of aminated coumarins for biological screening.

AB - The palladium-catalyzed nucleophilic substitution of (coumarinyl)methyl acetates is described. The reaction proceeds though a palladium ?-benzyl-like complex and allows for many different types of C-, N-, and S-nucleophiles to be regioselectively added to the biologically active coumarin motif. This new method was utilized to prepare a 128-membered library of aminated coumarins for biological screening.

KW - Benzylation

KW - Catalysis

KW - Chemical diversity

KW - Coumarin

KW - Decarboxylative

KW - Palladium

KW - Substitution

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DO - 10.3762/bjoc.8.133

M3 - Article

AN - SCOPUS:84864420058

SN - 1860-5397

VL - 8

SP - 1200

EP - 1207

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles

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Keywords

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