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  Deaminative chlorination of aminoheterocycles

Ghiazza, C., Faber, T., Gómez‐Palomino, A., & Cornella, J. (2022). Deaminative chlorination of aminoheterocycles. Nature Chemistry, 14(1), 78-84. doi:10.1038/s41557-021-00812-0.

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 Creators:
Ghiazza, Clément1, Author              
Faber, Teresa1, Author              
Gómez‐Palomino, Alejandro1, Author              
Cornella, Josep1, Author              
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1Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2466693              

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 Abstract: Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)‒NH2 can be converted into C(sp2)‒Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enables practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents.

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Language(s): eng - English
 Dates: 2021-03-302021-09-132021-12-162022-01-01
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1038/s41557-021-00812-0
 Degree: -

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Title: Nature Chemistry
  Abbreviation : Nat. Chem.
Source Genre: Journal
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Publ. Info: London, UK : Nature Publishing Group
Pages: - Volume / Issue: 14 (1) Sequence Number: - Start / End Page: 78 - 84 Identifier: ISSN: 1755-4330
CoNE: https://pure.mpg.de/cone/journals/resource/1755-4330