A C-3-Selective Direct Alkylation of Coumarins by Using a Microwave-Assisted Xanthate-Based Radical Reaction

Luis D. Miranda; Estefanía Icelo-Ávila; Ángel Rentería-Gómez; Michell Pila; Joaquín G. Marrero

doi:10.1002/ejoc.201500322

A C-3-Selective Direct Alkylation of Coumarins by Using a Microwave-Assisted Xanthate-Based Radical Reaction

Luis D. Miranda, Estefanía Icelo-Ávila, Ángel Rentería-Gómez, Michell Pila, Joaquín G. Marrero

Unidad Profesional Interdisciplinaria de Ingeniería, Campus Guanajuato (UPIIG)

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

13 Scopus citations

Abstract

A xanthate-based oxidative radical process for the direct alkylation of the coumarin ring system is presented. In the reaction, a vinylic and unactivated C–H bond of the coumarin system is replaced by an α-acyl functionality under neutral conditions. This reaction has a high reaction site selectivity, which can realize alkylation at the C-3 position.

Original language	English
Pages (from-to)	4098-4101
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	19
DOIs	https://doi.org/10.1002/ejoc.201500322
State	Published - Jul 2015

Keywords

Alkylation
Coumarin
C–H substitution
Radical reactions
Xanthate

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10.1002/ejoc.201500322

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title = "A C-3-Selective Direct Alkylation of Coumarins by Using a Microwave-Assisted Xanthate-Based Radical Reaction",

abstract = "A xanthate-based oxidative radical process for the direct alkylation of the coumarin ring system is presented. In the reaction, a vinylic and unactivated C–H bond of the coumarin system is replaced by an α-acyl functionality under neutral conditions. This reaction has a high reaction site selectivity, which can realize alkylation at the C-3 position.",

keywords = "Alkylation, Coumarin, C–H substitution, Radical reactions, Xanthate",

author = "Miranda, {Luis D.} and Estefan{\'i}a Icelo-{\'A}vila and {\'A}ngel Renter{\'i}a-G{\'o}mez and Michell Pila and Marrero, {Joaqu{\'i}n G.}",

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doi = "10.1002/ejoc.201500322",

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T1 - A C-3-Selective Direct Alkylation of Coumarins by Using a Microwave-Assisted Xanthate-Based Radical Reaction

AU - Miranda, Luis D.

AU - Icelo-Ávila, Estefanía

AU - Rentería-Gómez, Ángel

AU - Pila, Michell

AU - Marrero, Joaquín G.

PY - 2015/7

Y1 - 2015/7

N2 - A xanthate-based oxidative radical process for the direct alkylation of the coumarin ring system is presented. In the reaction, a vinylic and unactivated C–H bond of the coumarin system is replaced by an α-acyl functionality under neutral conditions. This reaction has a high reaction site selectivity, which can realize alkylation at the C-3 position.

AB - A xanthate-based oxidative radical process for the direct alkylation of the coumarin ring system is presented. In the reaction, a vinylic and unactivated C–H bond of the coumarin system is replaced by an α-acyl functionality under neutral conditions. This reaction has a high reaction site selectivity, which can realize alkylation at the C-3 position.

KW - Alkylation

KW - Coumarin

KW - C–H substitution

KW - Radical reactions

KW - Xanthate

UR - http://www.scopus.com/inward/record.url?scp=85027921175&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201500322

DO - 10.1002/ejoc.201500322

M3 - Artículo

SN - 1434-193X

VL - 2015

SP - 4098

EP - 4101

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 19

ER -

A C-3-Selective Direct Alkylation of Coumarins by Using a Microwave-Assisted Xanthate-Based Radical Reaction

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Keywords

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