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

Beatrice Lansbergen; Srija Tewari; Ireneusz Tomczyk; Maik Seemann; Henning Louis Buchholz; Mike Rippegarten; Daniel Chamier Cieminski; Fabio Juliá; Tobias Ritter

doi:10.1002/anie.202313659

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

Angew Chem Int Ed Engl. 2023 Dec 21;62(52):e202313659. doi: 10.1002/anie.202313659. Epub 2023 Nov 23.

Authors

Affiliations

¹ Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.
² Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

PMID: 37966018
DOI: 10.1002/anie.202313659

Abstract

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 L_n Pd^II (vinyl) complex formed after oxidative addition before it undergoes undesired homocoupling to form butadiene.

Keywords: Alkylation; Late Stage Functionalization; Reductive Electrophile Cross-Coupling; Vinyl Thianthrenium Salt.