Double and Single Hydroboration of Nitriles Catalyzed by a Ruthenium-Bis(silyl)xanthene Complex: Application to One-Pot Synthesis of Diarylamines and N-Arylimines

Takeo Kitano, Takashi Komuro, Hiromi Tobita

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

A ruthenium complex bearing a bis(silyl)xanthene chelate ligand xantsil, i.e. Ru[κ 3 (Si,O,Si)-xantsil](CO)(PCyp 3 ) (1a, Cyp = cyclopentyl), was found to catalyze both double and single hydroboration reactions of nitriles with pinacolborane (HBpin) and 9-borabicyclo[3.3.1]nonane (9-BBN) to give bis(boryl)amines 2 and N-borylimines 3, respectively, in mostly >99% yields. By combination of these reactions with subsequent palladium-catalyzed deborylative C-N coupling reactions of 2 and 3 with a 1:1 mixture of bromoarenes and KO t Bu, one-pot synthetic routes to tertiary N,N-diarylamines 4 and N-arylaldimines 5 from nitriles were developed.

Original languageEnglish
Pages (from-to)1417-1420
Number of pages4
JournalOrganometallics
Volume38
Issue number7
DOIs
Publication statusPublished - 2019 Apr 8

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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