Bis(imino)pyridine cobalt-catalyzed alkene isomerization-hydroboration: A strategy for remote hydrofunctionalization with terminal selectivity

Jennifer V. Obligacion, Paul J. Chirik

Research output: Contribution to journalArticle

190 Scopus citations

Abstract

Bis(imino)pyridine cobalt methyl complexes are active for the catalytic hydroboration of terminal, geminal, disubstituted internal, tri- and tetrasubstituted alkenes using pinacolborane (HBPin). The most active cobalt catalyst was obtained by introducing a pyrrolidinyl substituent into the 4-position of the bis(imino)pyridine chelate, enabling the facile hydroboration of sterically hindered substrates such as 1-methylcyclohexene, α-pinene, and 2,3-dimethyl-2-butene. Notably, these hydroboration reactions proceed with high activity and anti-Markovnikov selectivity in neat substrates at 23 C. With internal olefins, the cobalt catalyst places the boron substituent exclusively at the terminal positions of an alkyl chain, providing a convenient method for hydrofunctionalization of remote C-H bonds.

Original languageEnglish (US)
Pages (from-to)19107-19110
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number51
DOIs
StatePublished - Dec 26 2013

All Science Journal Classification (ASJC) codes

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

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