Modular functionalization of arenes in a triply selective sequence

rapid C(sp2) and C(sp3) coupling of C−Br, C−OTf, and C−Cl bonds enabled by a single palladium(I) dimer

Sinead T. Keaveney, Gourab Kundu, Franziska Schoenebeck*

*Corresponding author for this work

Research output: Contribution to journalArticle

33 Citations (Scopus)
20 Downloads (Pure)

Abstract

Full control over multiple competing coupling sites would enable straightforward access to densely functionalized compound libraries. Historically, the site selection in Pd0-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 PdI 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.

Original languageEnglish
Pages (from-to)12573-12577
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number38
DOIs
Publication statusPublished - 17 Sep 2018
Externally publishedYes

Bibliographical note

Copyright the Author(s) 2018. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

Keywords

  • arenes
  • C−C coupling
  • chemoselectivity
  • homogeneous catalysis
  • palladium(I) dimer

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