Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 38, Pages 12573-12577Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201808386
Keywords
arenes; C-C coupling; chemoselectivity; homogeneous catalysis; palladium(I) dimer
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Funding
- RWTH Aachen University
- European Research Council [ERC-637993]
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Full control over multiple competing coupling sites would enable straightforward access to densely functionalized compound libraries. Historically, the site selection in Pd-0-catalyzed functionalizations of poly(pseudo)halogenated arenes has been unpredictable, being dependent on the employed catalyst, the reaction conditions, and the substrate itself. Building on our previous report of C-Br-selective functionalization in the presence of C-OTf and C-Cl bonds, we herein complete the sequence and demonstrate the first general arylations and alkylations of C-OTf bonds (in <10 min), followed by functionalization of the C-Cl site (in < 25 min), at room temperature using the same air- and moisture-stable Pd-I dimer. This allowed the realization of the first general and triply selective sequential C-C coupling (in 2D and 3D space) of C-Br followed by C-OTf and then C-Cl bonds.
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