Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals

Vittorio Pace; Azzura Pelosi; Daniele Antermite; Ornelio Rosati; Massimo Curini; Wolfgang Holzer

doi:10.1039/c5cc10280d

Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals

Vittorio Pace (Corresponding author), Azzura Pelosi, Daniele Antermite, Ornelio Rosati, Massimo Curini, Wolfgang Holzer

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

An efficient, chemoselective homologation of disulfides and diselenides to the corresponding dithio- and diselenoacetals has been developed via the addition of bromomethyllithium. Chemoselectivity is fully preserved in the presence of concomitant electrophilic sites decorating the substrates. The synthetic potential of selected dithioacetals has been evaluated in Feringa–Fañanas-Mastral-type Pd-catalyzed coupling with an organolithium and in the unusual 1,4-addition to a Weinreb amide.

Original language	English
Pages (from-to)	2639-2642
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	12
DOIs	https://doi.org/10.1039/c5cc10280d
Publication status	Published - 2016

Austrian Fields of Science 2012

104015 Organic chemistry

Keywords

ALPHA'-CHLOROMETHYLKETONE DERIVATIVES
REAGENT-CONTROLLED HOMOLOGATION
LITHIUM-CHLORIDE CARBENOIDS
CHIRAL CALCIUM COMPLEXES
ASSEMBLY-LINE SYNTHESIS
MAGNESIUM CARBENOIDS
EFFICIENT SYNTHESIS
CARBONYL-COMPOUNDS
WEINREB AMIDES
BORONIC ESTERS

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10.1039/c5cc10280d

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title = "Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals",

abstract = "An efficient, chemoselective homologation of disulfides and diselenides to the corresponding dithio- and diselenoacetals has been developed via the addition of bromomethyllithium. Chemoselectivity is fully preserved in the presence of concomitant electrophilic sites decorating the substrates. The synthetic potential of selected dithioacetals has been evaluated in Feringa–Fa{\~n}anas-Mastral-type Pd-catalyzed coupling with an organolithium and in the unusual 1,4-addition to a Weinreb amide.",

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author = "Vittorio Pace and Azzura Pelosi and Daniele Antermite and Ornelio Rosati and Massimo Curini and Wolfgang Holzer",

year = "2016",

doi = "10.1039/c5cc10280d",

language = "English",

volume = "52",

pages = "2639--2642",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "ROYAL SOC CHEMISTRY",

number = "12",

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TY - JOUR

T1 - Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals

AU - Pace, Vittorio

AU - Pelosi, Azzura

AU - Antermite, Daniele

AU - Rosati, Ornelio

AU - Curini, Massimo

AU - Holzer, Wolfgang

PY - 2016

Y1 - 2016

N2 - An efficient, chemoselective homologation of disulfides and diselenides to the corresponding dithio- and diselenoacetals has been developed via the addition of bromomethyllithium. Chemoselectivity is fully preserved in the presence of concomitant electrophilic sites decorating the substrates. The synthetic potential of selected dithioacetals has been evaluated in Feringa–Fañanas-Mastral-type Pd-catalyzed coupling with an organolithium and in the unusual 1,4-addition to a Weinreb amide.

AB - An efficient, chemoselective homologation of disulfides and diselenides to the corresponding dithio- and diselenoacetals has been developed via the addition of bromomethyllithium. Chemoselectivity is fully preserved in the presence of concomitant electrophilic sites decorating the substrates. The synthetic potential of selected dithioacetals has been evaluated in Feringa–Fañanas-Mastral-type Pd-catalyzed coupling with an organolithium and in the unusual 1,4-addition to a Weinreb amide.

KW - ALPHA'-CHLOROMETHYLKETONE DERIVATIVES

KW - REAGENT-CONTROLLED HOMOLOGATION

KW - LITHIUM-CHLORIDE CARBENOIDS

KW - CHIRAL CALCIUM COMPLEXES

KW - ASSEMBLY-LINE SYNTHESIS

KW - MAGNESIUM CARBENOIDS

KW - EFFICIENT SYNTHESIS

KW - CARBONYL-COMPOUNDS

KW - WEINREB AMIDES

KW - BORONIC ESTERS

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U2 - 10.1039/c5cc10280d

DO - 10.1039/c5cc10280d

M3 - Article

AN - SCOPUS:84957569810

SN - 1359-7345

VL - 52

SP - 2639

EP - 2642

JO - Chemical Communications

JF - Chemical Communications

IS - 12

ER -

Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals

Abstract

Austrian Fields of Science 2012

Keywords

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