Nucleophilic ortho-propargylation of aryl sulfoxides: An interrupted pummerer/allenyl thio-Claisen rearrangement sequence

Andrew J. Eberhart; David J. Procter

doi:10.1002/anie.201300223

Nucleophilic ortho-propargylation of aryl sulfoxides: An interrupted pummerer/allenyl thio-Claisen rearrangement sequence

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Abstract

A new direction: The nucleophilic ortho-propargylation of aryl sulfoxides exploits intermolecular delivery of the nucleophile to sulfur followed by an intramolecular relay to carbon (see scheme). The simple, metal-free procedure is general, regiospecific with regard to the propargyl nucleophile, and completely selective for products of ortho-propargylation over allenylation. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English
Pages (from-to)	4008-4011
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	14
DOIs	https://doi.org/10.1002/anie.201300223
Publication status	Published - 2 Apr 2013

Keywords

arylsulfoxide
propargylation
Pummerer reaction
silane
thio-Claisen

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10.1002/anie.201300223

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abstract = "A new direction: The nucleophilic ortho-propargylation of aryl sulfoxides exploits intermolecular delivery of the nucleophile to sulfur followed by an intramolecular relay to carbon (see scheme). The simple, metal-free procedure is general, regiospecific with regard to the propargyl nucleophile, and completely selective for products of ortho-propargylation over allenylation. {\textcopyright} 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

keywords = "arylsulfoxide, propargylation, Pummerer reaction, silane, thio-Claisen",

author = "Eberhart, {Andrew J.} and Procter, {David J.}",

year = "2013",

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doi = "10.1002/anie.201300223",

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T1 - Nucleophilic ortho-propargylation of aryl sulfoxides: An interrupted pummerer/allenyl thio-Claisen rearrangement sequence

AU - Eberhart, Andrew J.

AU - Procter, David J.

PY - 2013/4/2

Y1 - 2013/4/2

N2 - A new direction: The nucleophilic ortho-propargylation of aryl sulfoxides exploits intermolecular delivery of the nucleophile to sulfur followed by an intramolecular relay to carbon (see scheme). The simple, metal-free procedure is general, regiospecific with regard to the propargyl nucleophile, and completely selective for products of ortho-propargylation over allenylation. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - A new direction: The nucleophilic ortho-propargylation of aryl sulfoxides exploits intermolecular delivery of the nucleophile to sulfur followed by an intramolecular relay to carbon (see scheme). The simple, metal-free procedure is general, regiospecific with regard to the propargyl nucleophile, and completely selective for products of ortho-propargylation over allenylation. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KW - arylsulfoxide

KW - propargylation

KW - Pummerer reaction

KW - silane

KW - thio-Claisen

U2 - 10.1002/anie.201300223

DO - 10.1002/anie.201300223

M3 - Article

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VL - 52

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 14

ER -

Nucleophilic ortho-propargylation of aryl sulfoxides: An interrupted pummerer/allenyl thio-Claisen rearrangement sequence

Abstract

Keywords

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