Insights into a Chemoselective Cobalt Catalyst for the Hydroboration of Alkenes and Nitriles

Abdulrahman D. Ibrahim, Steven W. Entsminger, Alison R. Fout

Research output: Contribution to journalArticlepeer-review

Abstract

A chemoselective hydroboration protocol with terminal alkene substrates is reported using an electron-rich, low-valent cobalt pincer compound. The process is catalytic and leads to exclusive formation of anti-Markovnikov products, tolerating amino groups, esters, epoxides, ketones, and other functionalities. The protocol was successfully extended toward the hydroboration of nitriles, generating the corresponding amines in moderate to good yields. Labeling studies with deuterated pinacolborane gave insights into the mechanism, establishing the intermediacy of a cobalt hydride, as well as an insertion, β-hydride elimination, and alkene isomerization pathway. These insights provide a rationale for the observed regioselectivity and allow us to propose a catalytic mechanism.

Original languageEnglish (US)
Pages (from-to)3730-3734
Number of pages5
JournalACS Catalysis
Volume7
Issue number5
DOIs
StatePublished - May 5 2017

Keywords

  • alkene
  • catalysis
  • chemoselective
  • cobalt
  • hydroboration
  • nitrile

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint

Dive into the research topics of 'Insights into a Chemoselective Cobalt Catalyst for the Hydroboration of Alkenes and Nitriles'. Together they form a unique fingerprint.

Cite this