Thiol-promoted selective addition of ketones to aldehydes

Regev Parnes; Sachin Narute; Doron Pappo

doi:10.1021/ol502937n

Thiol-promoted selective addition of ketones to aldehydes

Regev Parnes, Sachin Narute, Doron Pappo

Department of Chemistry

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

13 Scopus citations

Abstract

A simple and efficient thiol-mediated addition of ketones to aromatic and aliphatic aldehydes is reported. This thermodynamically controlled Pummerer/aldol reaction, which can tolerate both moisture and protic functional groups, provides a direct entry to syn-β-thioketones in high chemo- and regioselectivity. Mechanistic studies revealed that selective transformation of the aldehyde to an electrophilic thionium ion species concurrent with the generation of a nucleophilic vinyl sulfide coupling partner from the ketone is imposing cross-coupling over dimerization.

Original language	English
Pages (from-to)	5922-5925
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	22
DOIs	https://doi.org/10.1021/ol502937n
State	Published - 21 Nov 2014

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol502937n

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title = "Thiol-promoted selective addition of ketones to aldehydes",

abstract = "A simple and efficient thiol-mediated addition of ketones to aromatic and aliphatic aldehydes is reported. This thermodynamically controlled Pummerer/aldol reaction, which can tolerate both moisture and protic functional groups, provides a direct entry to syn-β-thioketones in high chemo- and regioselectivity. Mechanistic studies revealed that selective transformation of the aldehyde to an electrophilic thionium ion species concurrent with the generation of a nucleophilic vinyl sulfide coupling partner from the ketone is imposing cross-coupling over dimerization.",

author = "Regev Parnes and Sachin Narute and Doron Pappo",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

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AU - Parnes, Regev

AU - Narute, Sachin

AU - Pappo, Doron

PY - 2014/11/21

Y1 - 2014/11/21

N2 - A simple and efficient thiol-mediated addition of ketones to aromatic and aliphatic aldehydes is reported. This thermodynamically controlled Pummerer/aldol reaction, which can tolerate both moisture and protic functional groups, provides a direct entry to syn-β-thioketones in high chemo- and regioselectivity. Mechanistic studies revealed that selective transformation of the aldehyde to an electrophilic thionium ion species concurrent with the generation of a nucleophilic vinyl sulfide coupling partner from the ketone is imposing cross-coupling over dimerization.

AB - A simple and efficient thiol-mediated addition of ketones to aromatic and aliphatic aldehydes is reported. This thermodynamically controlled Pummerer/aldol reaction, which can tolerate both moisture and protic functional groups, provides a direct entry to syn-β-thioketones in high chemo- and regioselectivity. Mechanistic studies revealed that selective transformation of the aldehyde to an electrophilic thionium ion species concurrent with the generation of a nucleophilic vinyl sulfide coupling partner from the ketone is imposing cross-coupling over dimerization.

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U2 - 10.1021/ol502937n

DO - 10.1021/ol502937n

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JO - Organic Letters

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Thiol-promoted selective addition of ketones to aldehydes

Abstract

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