Orthogonal Olefination with Organogermanes

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. The site- and E-selective coupling of aryl germanes with alkenes over (pseudo)halogens (C-I, C-Br, C-Cl, C-F, C-OTf, C-OSO2F), silanes and boronic acid derivatives is reported. This unprecedented [Ge]-based oxidative Heck coupling proceeds at room temperature with high speed and under air-tolerant and base-free conditions.+image

Automated summary

A novel [Ge]-based oxidative Heck coupling reaction is reported, which allows for the site- and E-selective coupling of aryl germanes with alkenes. The reaction proceeds rapidly at room temperature and is tolerant of commonly used coupling handles and alternative functionalities.