Efficient O-Acylation of Alcohols and Phenol Using Cp2TiCl as a Reaction Promoter

A method has been developed for the conversion of primary, secondary, and tertiary alcohols, and phenol, into the corresponding esters at room temperature. The method uses a titanium(III) species generated from a substoichiometric amount of titanocene dichloride together with manganese(0) as a reduc...

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Bibliographic Details
Published in:European journal of organic chemistry 2016-07, Vol.2016 (21), p.3584-3591
Main Authors: Durán-Peña, María Jesús, Botubol-Ares, José Manuel, Hanson, James R., Hernández-Galán, Rosario, Collado, Isidro G.
Format: Article
Language:English
Subjects:
Acylation
Alcohol
Esters
Halohydrins
Phenols
Radical reactions
Titanium
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Summary:A method has been developed for the conversion of primary, secondary, and tertiary alcohols, and phenol, into the corresponding esters at room temperature. The method uses a titanium(III) species generated from a substoichiometric amount of titanocene dichloride together with manganese(0) as a reductant, as well as methylene diiodide. It involves a transesterification from an ethyl ester, or a reaction with an acyl chloride. A radical mechanism is proposed for these transformations. A set of primary, secondary, and tertiary alcohols, and phenol, have been converted into the corresponding esters using a substoichiometric amount of bis(cyclopentadienyl)titanium(III) chloride in good yields and under mild reaction conditions.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600496