Highly efficient and enantioselective hydrogenation of quinolines and pyridines with Ir-Difluorphos catalyst

Weijun Tang, Yawei Sun, Xu Lijin, Tianli Wang, Fan Qinghua Fan, Kim Hung Lam, Albert S.C. Chan

Research output: Journal article publicationJournal articleAcademic researchpeer-review

78 Citations (Scopus)

Abstract

The combination of the readily available chiral bisphosphine ligand Difluorphos with [Ir(COD)Cl]2 in THF resulted in a highly efficient catalyst system for asymmetric hydrogenation of quinolines at quite low catalyst loadings (0.05-0.002 mol%), affording the corresponding products with high enantioselectivities (up to 96%), excellent catalytic activities (TOF up to 3510 h-1) and productivities (TON up to 43000). The same catalyst was also successfully applied to the asymmetric hydrogenation of trisubstituted pyridines with nearly quantitative yields and up to 98% ee. In these two reactions, the addition of I2 additive is indispensable; but the amount of I2 has a different effect on catalytic performance.

Original languageEnglish
Pages (from-to)3464-3471
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number15
DOIs
Publication statusPublished - 7 Aug 2010

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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