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  Selective Functionalization of Aminoheterocycles by a Pyrylium Salt

Moser, D., Duan, Y., Ma, Y., O'Neill, M. J., & Cornella, J. (2018). Selective Functionalization of Aminoheterocycles by a Pyrylium Salt. Angewandte Chemie, International Edition, 57(34), 11035-11039. doi:10.1002/anie.201806271.

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Genre: Journal Article

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 Creators:
Moser, Daniel1, Author              
Duan, Yaya1, Author              
Ma, Yuanhong1, Author              
O'Neill, Matthew J.1, Author              
Cornella, Josep1, Author              
Affiliations:
1Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2466693              

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Free keywords: amination; C‒N activation; heterocycles; late-stage functionalization; pyrylium
 Abstract: The functionalization of aminoheterocycles via a pyrylium tetrafluoroborate reagent (Pyry‐BF4) is presented. This reagent efficiently condenses with a great variety of heterocyclic amines and primes the C‒N bond for nucleophilic aromatic substitution. More than 60 examples of C‒O, C‒N, C‒S or C‒SO2R are disclosed herein. In contrast to C‒N activation via diazotization and polyalkylation, this method is characterized by its mild conditions and impressive functional group tolerance. In addition to small molecule derivatization, Pyry‐BF4 allows for the introduction of functional groups in a late‐stage fashion to furnish highly functionalized structures.

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Language(s): eng - English
 Dates: 2018-05-312018-07-032018-08-20
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201806271
 Degree: -

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Title: Angewandte Chemie, International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 57 (34) Sequence Number: - Start / End Page: 11035 - 11039 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851