Literature DB >> 26750866

Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals.

Vittorio Pace1, Azzurra Pelosi, Daniele Antermite, Ornelio Rosati, Massimo Curini, Wolfgang Holzer.   

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.

Entities:  

Year:  2016        PMID： 26750866     DOI： 10.1039/c5cc10280d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  5 in total

1.  Consecutive and Selective Double Methylene Insertion of Lithium Carbenoids to Isothiocyanates: A Direct Assembly of Four-Membered Sulfur-Containing Cycles.

Authors:  Raffaele Senatore; Monika Malik; Thierry Langer; Wolfgang Holzer; Vittorio Pace
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-13       Impact factor: 16.823

Review 2.  Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry.

Authors:  Serena Monticelli; Laura Castoldi; Irene Murgia; Raffaele Senatore; Eugenia Mazzeo; Judith Wackerlig; Ernst Urban; Thierry Langer; Vittorio Pace
Journal:  Monatsh Chem       Date:  2016-12-07       Impact factor: 1.451

3.  A practical guide for using lithium halocarbenoids in homologation reactions.

Authors:  Serena Monticelli; Marta Rui; Laura Castoldi; Giada Missere; Vittorio Pace
Journal:  Monatsh Chem       Date:  2018-06-11       Impact factor: 1.451

4.  Sustainable Asymmetric Organolithium Chemistry: Enantio- and Chemoselective Acylations through Recycling of Solvent, Sparteine, and Weinreb "Amine".

Authors:  Serena Monticelli; Wolfgang Holzer; Thierry Langer; Alexander Roller; Berit Olofsson; Vittorio Pace
Journal:  ChemSusChem       Date:  2019-02-13       Impact factor: 8.928

5.  Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes.

Authors:  Margherita Miele; Andrea Citarella; Thierry Langer; Ernst Urban; Martin Zehl; Wolfgang Holzer; Laura Ielo; Vittorio Pace
Journal:  Org Lett       Date:  2020-09-10       Impact factor: 6.005
  5 in total

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