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  Regio- and Stereoselective Chlorocyanation of Alkynes

Barrado, A. G., Zielinski, A., Alcarazo, M., & Goddard, R. (2017). Regio- and Stereoselective Chlorocyanation of Alkynes. Angewandte Chemie, International Edition in English, 56(43), 13401-13405. doi:10.1002/anie.201705851.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-002E-3180-D Version Permalink: https://hdl.handle.net/11858/00-001M-0000-002E-3181-B
Genre: Journal Article

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 Creators:
Barrado, Alejandro G.1, Author
Zielinski, Adam1, Author
Alcarazo, Manuel1, Author
Goddard, Richard2, Author           
Affiliations:
1Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen , Tammannstrasse 2, 37077 Göttingen, Germany, ou_persistent22              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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 Abstract: A variety of terminal and internal alkynes were converted regio- and stereoselectively into (Z)-3-chloroacrylonitriles by treatment with BCl3 in the presence of stoichiometric amounts of imidazolium thiocyanates. These products could be readily functionalized to provide useful building blocks, thus demonstrating the synthetic value of the method. Preliminary mechanistic studies suggest initial activation of the cationic thiocyanate by the Lewis acid, followed by electrophilic attack of the alkyne. The syn addition of a chloride to the vinyl cation intermediate and final elimination of the thiourea unit afford the desired chloroacrylonitriles.

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Language(s): eng - English
 Dates: 2017-06-082017-08-172017-09-212017-10-11
 Publication Status: Issued
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201705851
 Degree: -

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Title: Angewandte Chemie, International Edition in English
  Other : Angewandte Chemie International Edition in English
  Abbreviation : Angew. Chem., Int. Ed. Engl.
  Abbreviation : Angew. Chem. Int. Ed. Engl.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: 5 Volume / Issue: 56 (43) Sequence Number: - Start / End Page: 13401 - 13405 Identifier: ISSN: 0570-0833
CoNE: https://pure.mpg.de/cone/journals/resource/0570-0833