O-arylative Passerini reactions

Laurent El Kaim; Marie Gizolme; Laurence Grimaud

doi:10.1021/ol0617502

O-arylative Passerini reactions

Laurent El Kaim
, Marie Gizolme
, Laurence Grimaud

Unité Chimie et Procédés

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

Abstract

(Chemical Equation Presented) The three-component addition of isocyanides to phenol derivatives and aldehydes proceeds easily in methanol to form O-arylated compounds in a new Passerini-type reaction. The key step of the conversion lies in an irreversible Smiles rearrangement of intermediate phenoxyimidate adducts. It represents the first use of a Smiles rearrangement in a Passerini reaction.

Original language	English
Pages (from-to)	5021-5023
Number of pages	3
Journal	Organic Letters
Volume	8
Issue number	22
DOIs	https://doi.org/10.1021/ol0617502
Publication status	Published - 26 Oct 2006
Externally published	Yes

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10.1021/ol0617502

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title = "O-arylative Passerini reactions",

abstract = "(Chemical Equation Presented) The three-component addition of isocyanides to phenol derivatives and aldehydes proceeds easily in methanol to form O-arylated compounds in a new Passerini-type reaction. The key step of the conversion lies in an irreversible Smiles rearrangement of intermediate phenoxyimidate adducts. It represents the first use of a Smiles rearrangement in a Passerini reaction.",

author = "\{El Kaim\}, Laurent and Marie Gizolme and Laurence Grimaud",

year = "2006",

month = oct,

day = "26",

doi = "10.1021/ol0617502",

language = "English",

volume = "8",

pages = "5021--5023",

journal = "Organic Letters",

issn = "1523-7060",

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T1 - O-arylative Passerini reactions

AU - El Kaim, Laurent

AU - Gizolme, Marie

AU - Grimaud, Laurence

PY - 2006/10/26

Y1 - 2006/10/26

N2 - (Chemical Equation Presented) The three-component addition of isocyanides to phenol derivatives and aldehydes proceeds easily in methanol to form O-arylated compounds in a new Passerini-type reaction. The key step of the conversion lies in an irreversible Smiles rearrangement of intermediate phenoxyimidate adducts. It represents the first use of a Smiles rearrangement in a Passerini reaction.

AB - (Chemical Equation Presented) The three-component addition of isocyanides to phenol derivatives and aldehydes proceeds easily in methanol to form O-arylated compounds in a new Passerini-type reaction. The key step of the conversion lies in an irreversible Smiles rearrangement of intermediate phenoxyimidate adducts. It represents the first use of a Smiles rearrangement in a Passerini reaction.

U2 - 10.1021/ol0617502

DO - 10.1021/ol0617502

M3 - Article

AN - SCOPUS:33750929343

SN - 1523-7060

VL - 8

SP - 5021

EP - 5023

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

O-arylative Passerini reactions

Abstract

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