Orthogonal Olefination with Organogermanes

Angewandte Chemie International Edition, vol. 62, pp. e202310380

Abstract

Abstract Reported herein is a fully orthogonal olefination, which involves the site‐ and E‐selective coupling of aryl germanes with alkenes, tolerating otherwise widely employed coupling handles such as aromatic (pseudo)halogens (C−I, C−Br, C−Cl, C−F, C−OTf, C−OSO2F), silanes and boronic acid derivatives as well as alternative functionalities. This unprecedented [Ge]‐based oxidative Heck coupling proceeds at room temperature with high speed (10 min to 2 hours) and operational simplicity owing to its base‐free and air‐tolerant features.

Authors 3

1. Amit Dahiya Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 52074 Aachen Germany

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 52074 Aachen Germany

2. Markus D. Schoetz Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 52074 Aachen Germany

   RWTH Aachen University: Rheinisch-Westfalische Technische Hochschule Aachen, Chemistry, GERMANY

3. Franziska Schoenebeck corresponding Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 52074 Aachen Germany

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 52074 Aachen Germany