Stereo‐ and Regioselective Alkyne Hydrometallation with Gold (III) Hydrides

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Abstract: The hydroauration of internal and terminal alkynes by gold (III) hydride complexes [(C^N^C) AuH] was found to be mediated by radicals and proceeds by an unexpected binuclear outer‐sphere mechanism to cleanly form trans‐insertion products. Radical precursors such as azobisisobutyronitrile lead to a drastic rate enhancement. DFT calculations support the proposed radical mechanism, with very low activation barriers, and rule out mononuclear mechanistic alternatives. These alkyne hydroaurations are highly regio‐ and stereospecific for the formation of Z‐vinyl isomers, with Z/E ratios of >99:1 in most cases.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Stereo‐ and Regioselective Alkyne Hydrometallation with Gold (III) Hydrides ; volume:128 ; number:40 ; year:2016 ; pages:12509-12512 ; extent:4
Angewandte Chemie ; 128, Heft 40 (2016), 12509-12512 (gesamt 4)

Creator: Pintus, Anna
Rocchigiani, Luca
Fernandez‐Cestau, Julio
Budzelaar, Peter H. M.
Bochmann, Manfred

DOI: 10.1002/ange.201607522

URN: urn:nbn:de:101:1-2022101106324207485022

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:31 AM CEST

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Associated

Pintus, Anna
Rocchigiani, Luca
Fernandez‐Cestau, Julio
Budzelaar, Peter H. M.
Bochmann, Manfred

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