TY - JOUR
T1 - Titanium catalyzed reduction of aromatic halides by sodium borohydride
AU - Liu, Yumin
AU - Schwartz, Jeffrey
N1 - Funding Information:
Acknowledgements. The authors acknowledge support for this work given by Texas Eastern Transmission Corporation and by the National Science Foundation.
Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.
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.
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U2 - 10.1016/0040-4020(94)01134-L
DO - 10.1016/0040-4020(94)01134-L
M3 - Article
AN - SCOPUS:0028932907
SN - 0040-4020
VL - 51
SP - 4471
EP - 4482
JO - Tetrahedron
JF - Tetrahedron
IS - 15
ER -