Mechanistic Origins of Regioselectivity in Cobalt-Catalyzed C(sp2)-H Borylation of Benzoate Esters and Arylboronate Esters

Tyler P. Pabst, Linda Quach, Kaitlyn T. MacMillan, Paul J. Chirik

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Carbon–hydrogen (C–H) bonds are ubiquitous in organic molecules, and methods for their selective functionalization to more reactive functional groups is a long-standing goal in catalysis, as applied to organic synthesis. Of the established methods involving transition metal catalysts, many employ carefully engineered substrate-catalyst interactions, placing the targeted C–H bond proximal to the metal catalyst, resulting in activation and subsequent functionalization. Here, we report mechanistic investigations describing a conceptual alternative to this approach whereby a cobalt-based borylation catalyst differentiates between subtle electronic differences in C(sp2)-H bonds of benzoate esters and arylboronate esters. These advances motivate studies of catalysts that rely on inherent differences in C–H bond electronics to distinguish chemically inequivalent sites, providing a new tool for organic synthesis.

Original languageEnglish (US)
Pages (from-to)237-254
Number of pages18
JournalChem
Volume7
Issue number1
DOIs
StatePublished - Jan 14 2021

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Biochemistry
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Biochemistry, medical
  • Materials Chemistry

Keywords

  • C-H functionalization
  • SDG12: Responsible consumption and production
  • SDG3: Good health and well-being
  • boron
  • cobalt
  • site selective

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