Regiodivergent Carbonylation of Alkenes: Selective Palladium‐Catalyzed Synthesis of Linear and Branched Selenoesters

Author:

Cao Zhusong1,Wang Qiang1,Neumann Helfried1,Beller Matthias1ORCID

Affiliation:

1. Leibniz-Institut für Katalyse e.V.an der Universität Rostock Albert-Einstein-Straße 29a 18059 Rostock Germany

Abstract

AbstractAn unprecedented regiodivergent palladium‐catalyzed carbonylation of aromatic alkenes has been developed. Utilizing commercially available Pd(CH3CN)2Cl2 in the presence of 1,1′‐ferrocenediyl‐bis(tert‐butyl(pyridin‐2‐yl)phosphine) ligand L8 diverse selenoesters are obtained in a straightforward manner. Key to success for the control of the regioselectivity of the carbonylation step is the concentration of the acidic co‐catalyst. This general protocol features wide functional group compatibility and good regioselectivity. Mechanistic studies suggest that the presence of stoichiometric amounts of acid changes the properties and coordination mode of the ligand leading to reversed regioselectivity.

Funder

Alexander von Humboldt-Stiftung

Publisher

Wiley

Subject

General Medicine

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