Titanium catalyzed reduction of aromatic halides by sodium borohydride

Yumin Liu, Jeffrey Schwartz

Research output: Contribution to journalArticle

54 Scopus citations

Abstract

The reduction of aryl halides by sodium borohydride is catalyzed by titanium complexes; di(cyclopentadienyl)titanium dichloride (titanocene dichloride) is highly effective. The reaction scope and mechanism are solvent dependent. In dimethylformamide (DMF), an adduct of DMF and sodium borohydride is formed which reduces simple aryl halides by a non-radical, likely nucleophilic route. Dimethylamino- substituted products are formed, as are simple dechlorinated species. In dimethylacetamide or in ethers, a radical-based reaction involving activated titanocene borohydride takes place, and only dechlorinated products result.

Original languageEnglish (US)
Pages (from-to)4471-4482
Number of pages12
JournalTetrahedron
Volume51
Issue number15
DOIs
StatePublished - Apr 10 1995

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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