期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 42, 页码 18717-18722出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202008372
关键词
chemoselectivity; germanium; halogenation; reaction mechanisms; synthetic methods
资金
- RWTH Aachen University
- European Research Council
- Projekt DEAL
While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.
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