Reductive Cross‐Coupling of a Vinyl Thianthrenium Salt and Secondary Alkyl Iodides

We report the first reductive vinylation of alkyl iodides. The reaction uses a vinyl thianthrenium salt, a palladium catalyst, and an alkyl zinc intermediate formed in situ to trap the LnPdII(vinyl) complex formed after oxidative addition before it undergoes undesired homocoupling to form butadiene....

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Veröffentlicht in:	Angewandte Chemie International Edition 2023-12, Vol.62 (52), p.e202313659-n/a
Hauptverfasser:	Lansbergen, Beatrice, Tewari, Srija, Tomczyk, Ireneusz, Seemann, Maik, Buchholz, Henning Louis, Rippegarten, Mike, Cieminski, Daniel Chamier, Juliá, Fabio, Ritter, Tobias
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkylation Catalysts Cross coupling Iodides Late Stage Functionalization Palladium Reductive Electrophile Cross-Coupling Vinyl Thianthrenium Salt
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Beschreibung
Zusammenfassung:	We report the first reductive vinylation of alkyl iodides. The reaction uses a vinyl thianthrenium salt, a palladium catalyst, and an alkyl zinc intermediate formed in situ to trap the LnPdII(vinyl) complex formed after oxidative addition before it undergoes undesired homocoupling to form butadiene. Here we report an unprecedented reductive vinylation of alkyl iodides, which expands on the currently possible reductive Csp2‐Csp3 cross‐coupling reactions.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.202313659