Pd(II)-Catalyzed Synthesis of Benzocyclobutenes by β-Methylene-Selective C(sp3)-H Arylation with a Transient Directing Group

Philip A. Provencher, John F. Hoskin, Jonathan J. Wong, Xiangyang Chen, Jin Quan Yu, K. N. Houk, Erik J. Sorensen

Research output: Contribution to journalArticlepeer-review


Methylene-selective C-H functionalization is a significant hurdle that remains to be addressed in the field of Pd(II) catalysis. We report a Pd(II)-catalyzed synthesis of benzocyclobutenes by methylene-selective C(sp3)-H arylation of ketones. The reaction utilizes glycine as a transient directing group and a 2-pyridone ligand, which may govern the methylene selectivity by making intimate molecular associations with the substrate during concerted metalation-deprotonation. This reaction is shown to be highly selective for intramolecular methylene C(sp3)-H arylation, thus enabling sequential C(sp3)-H functionalization.

Original languageEnglish (US)
Pages (from-to)20035-20041
Number of pages7
JournalJournal of the American Chemical Society
Issue number48
StatePublished - Dec 8 2021

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry


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