Syntheses and Catalytic Hydrogenation Performance of Cationic Bis(phosphine) Cobalt(I) Diene and Arene Compounds

Hongyu Zhong, Max R. Friedfeld, Paul J. Chirik

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

Chloride abstraction from [(R,R)-(iPrDuPhos)Co(μ-Cl)]2 with NaBArF4 (BArF4=B[(3,5-(CF3)2)C6H3]4) in the presence of dienes, such as 1,5-cyclooctadiene (COD) or norbornadiene (NBD), yielded long sought-after cationic bis(phosphine) cobalt complexes, [(R,R)-(iPrDuPhos)Co(η22-diene)][BArF4]. The COD complex proved substitutionally labile undergoing diene substitution with tetrahydrofuran, NBD, or arenes. The resulting 18-electron, cationic cobalt(I) arene complexes, as well as the [(R,R)-(iPrDuPhos)Co(diene)][BArF4] derivatives, proved to be highly active and enantioselective precatalysts for asymmetric alkene hydrogenation. A cobalt–substrate complex, [(R,R)-(iPrDuPhos)Co(MAA)][BArF4] (MAA=methyl 2-acetamidoacrylate) was crystallographically characterized as the opposite diastereomer to that expected for productive hydrogenation demonstrating a Curtin–Hammett kinetic regime similar to rhodium catalysis.

Original languageEnglish (US)
Pages (from-to)9194-9198
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number27
DOIs
StatePublished - Jul 1 2019

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • alkene hydrogenation
  • asymmetric catalysis
  • catalyst–substrate complex
  • cobalt

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