Some Aspects of α-(Acyloxy)alkyl Radicals in Organic Synthesis †

Béatrice Quiclet-Sire; Samir Z. Zard

doi:10.3390/molecules28227561

Some Aspects of α-(Acyloxy)alkyl Radicals in Organic Synthesis †

Béatrice Quiclet-Sire
, Samir Z. Zard

Laboratoire de Synthèse Organique

Research output: Contribution to journal › Review article › peer-review

Abstract

The preparation and use of α-(acyloxy)alkyl xanthates to generate and capture α-(acyloxy)alkyl radicals is briefly reviewed. Their inter- and intramolecular additions to both activated and unactivated, electronically unbiased, alkenes, and to (hetero)aromatic rings, as well as their radical allylation and vinylation reactions are described. Application to the total synthesis of two 4-hydroxytetralone natural products is also presented.

Original language	English
Article number	7561
Journal	Molecules
Volume	28
Issue number	22
DOIs	https://doi.org/10.3390/molecules28227561
Publication status	Published - 1 Nov 2023
Externally published	Yes

Keywords

enones
radical additions
xanthates
α-(acyloxy)alkyl radicals

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10.3390/molecules28227561

Cite this

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title = "Some Aspects of α-(Acyloxy)alkyl Radicals in Organic Synthesis †",

abstract = "The preparation and use of α-(acyloxy)alkyl xanthates to generate and capture α-(acyloxy)alkyl radicals is briefly reviewed. Their inter- and intramolecular additions to both activated and unactivated, electronically unbiased, alkenes, and to (hetero)aromatic rings, as well as their radical allylation and vinylation reactions are described. Application to the total synthesis of two 4-hydroxytetralone natural products is also presented.",

keywords = "enones, radical additions, xanthates, α-(acyloxy)alkyl radicals",

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AU - Quiclet-Sire, Béatrice

AU - Zard, Samir Z.

PY - 2023/11/1

Y1 - 2023/11/1

N2 - The preparation and use of α-(acyloxy)alkyl xanthates to generate and capture α-(acyloxy)alkyl radicals is briefly reviewed. Their inter- and intramolecular additions to both activated and unactivated, electronically unbiased, alkenes, and to (hetero)aromatic rings, as well as their radical allylation and vinylation reactions are described. Application to the total synthesis of two 4-hydroxytetralone natural products is also presented.

AB - The preparation and use of α-(acyloxy)alkyl xanthates to generate and capture α-(acyloxy)alkyl radicals is briefly reviewed. Their inter- and intramolecular additions to both activated and unactivated, electronically unbiased, alkenes, and to (hetero)aromatic rings, as well as their radical allylation and vinylation reactions are described. Application to the total synthesis of two 4-hydroxytetralone natural products is also presented.

KW - enones

KW - radical additions

KW - xanthates

KW - α-(acyloxy)alkyl radicals

U2 - 10.3390/molecules28227561

DO - 10.3390/molecules28227561

M3 - Review article

C2 - 38005282

AN - SCOPUS:85177763028

SN - 1420-3049

VL - 28

JO - Molecules

JF - Molecules

IS - 22

M1 - 7561

ER -

Some Aspects of α-(Acyloxy)alkyl Radicals in Organic Synthesis †

Abstract

Keywords

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