Titanium catalyzed reduction of aromatic halides by sodium borohydride

Yumin Liu, Jeffrey Schwartz

Research output: Contribution to journalArticle

54 Citations (Scopus)

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

Fingerprint

Dimethylformamide
Titanium
Borohydrides
Ethers
sodium borohydride
titanocene
titanocene dichloride
dimethylacetamide

All Science Journal Classification (ASJC) codes

  • Drug Discovery
  • Biochemistry
  • Organic Chemistry

Cite this

@article{11a2b58d379646f893dfab2a98f96c3c,
title = "Titanium catalyzed reduction of aromatic halides by sodium borohydride",
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.",
author = "Yumin Liu and Jeffrey Schwartz",
year = "1995",
month = "4",
day = "10",
doi = "https://doi.org/10.1016/0040-4020(94)01134-L",
language = "English (US)",
volume = "51",
pages = "4471--4482",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "15",

}

Titanium catalyzed reduction of aromatic halides by sodium borohydride. / Liu, Yumin; Schwartz, Jeffrey.

In: Tetrahedron, Vol. 51, No. 15, 10.04.1995, p. 4471-4482.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Titanium catalyzed reduction of aromatic halides by sodium borohydride

AU - Liu, Yumin

AU - Schwartz, Jeffrey

PY - 1995/4/10

Y1 - 1995/4/10

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0028932907&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028932907&partnerID=8YFLogxK

U2 - https://doi.org/10.1016/0040-4020(94)01134-L

DO - https://doi.org/10.1016/0040-4020(94)01134-L

M3 - Article

VL - 51

SP - 4471

EP - 4482

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 15

ER -