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  Iridium‐Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis

Yu, P., Bismuto, A., & Morandi, B. (2020). Iridium‐Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis. Angewandte Chemie, International Edition, 59(7), 2904-2910. doi:10.1002/anie.201912803.

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Genre: Journal Article

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 Creators:
Yu, Peng1, 2, Author              
Bismuto, Alessandro1, Author
Morandi, Bill1, 2, Author              
Affiliations:
1Laboratorium für Organische Chemie ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093 Zürich, Switzerland, ou_persistent22              
2Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2040309              

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Free keywords: hydrobromination; hydrochlorination; iridium; shuttle catalysis; vinyl chloride
 Abstract: Described herein are two different methods for the synthesis of vinyl halides by a shuttle catalysis based iridium‐catalyzed transfer hydrohalogenation of unactivated alkynes. The use of 4‐chlorobutan‐2‐one or tert‐butyl halide as donors of hydrogen halides allows this transformation in the absence of corrosive reagents, such as hydrogen halides or acid chlorides, thus largely improving the functional‐group tolerance and safety profile of these reactions compared to the state‐of‐the‐art. This method has granted access to alkenyl halide compounds containing acid‐sensitive groups, such as tertiary alcohols, silyl ethers, and acetals. The synthetic value of those methodologies has been demonstrated by gram‐scale synthesis where low catalyst loading was achieved.

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Language(s): eng - English
 Dates: 2019-10-072019-11-262020-02-10
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201912803
 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: 59 (7) Sequence Number: - Start / End Page: 2904 - 2910 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851