Efficient O‐Acylation of Alcohols and Phenol Using Cp2TiCl as a Reaction Promoter. Issue 21 (4th July 2016)

• Record Type: Journal Article
• Authors: Durán‐Peña, María Jesús; Botubol‐Ares, José Manuel; Hanson, James R.; Hernández‐Galán, Rosario; Collado, Isidro G.
• Is Part Of: European journal of organic chemistry. Issue 21(2016)
• Page Start: 3584
• Page End: 3591
• Publication Date: 2016-07-04
• Subjects: Esters -- Acylation -- Radical reactions -- Halohydrins -- Titanium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600496
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : 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.