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  Catalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C−COCl Bond Cleavage

Denton, E. H., Lee, Y. H., Roediger, S., Boehm, P., Fellert, M., & Morandi, B. (2021). Catalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C−COCl Bond Cleavage. Angewandte Chemie International Edition, 60(43), 23435-23443. doi:10.1002/anie.202108818.

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 Creators:
Denton, Elliott H.1, Author
Lee, Yong Ho1, 2, Author              
Roediger, Sven1, Author
Boehm, Philip1, Author
Fellert, Maximilian1, 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: Acid chlorides; Carbonylation; CO-free; Difunctionalization; Palladium
 Abstract: Here we report a palladium-catalysed difunctionalisation of unsaturated C−C bonds with acid chlorides. Formally, the C−COCl bond of an acid chloride is cleaved and added, with complete atom economy, across either strained alkenes or a tethered alkyne to generate new acid chlorides. The transformation does not require exogenous carbon monoxide, operates under mild conditions, shows a good functional group tolerance, and gives the isolated products with excellent stereoselectivity. The intermolecular reaction tolerates both aryl- and alkenyl-substituted acid chlorides and is successful when carboxylic acids are transformed to the acid chloride in situ. The reaction also shows an example of temperature-dependent stereodivergence which, together with plausible mechanistic pathways, is investigated by DFT calculations. Moreover, we show that benzofurans can be formed in an intramolecular variant of the reaction. Finally, derivatisation of the products from the intermolecular reaction provides a highly stereoselective approach for the synthesis of tetrasubstituted cyclopentanes.

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Language(s): eng - English
 Dates: 2021-07-022021-08-252021-10-18
 Publication Status: Published in print
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202108818
 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: 60 (43) Sequence Number: - Start / End Page: 23435 - 23443 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851