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 journalArticlepeer-review

45 Citations (Scopus)
36 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

Fingerprint

Dive into the research topics of 'Modular functionalization of arenes in a triply selective sequence: rapid C(sp<sup>2</sup>) and C(sp<sup>3</sup>) coupling of C−Br, C−OTf, and C−Cl bonds enabled by a single palladium(I) dimer'. Together they form a unique fingerprint.

Cite this