An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols. Issue 7 (20th January 2016)

• Record Type: Journal Article
• Authors: Ren, Bo; Ramström, Olof; Zhang, Qiang; Ge, Jiantao; Dong, Hai
• Is Part Of: Chemistry. Volume 22:Issue 7(2016)
• Page Start: 2481
• Page End: 2486
• Publication Date: 2016-01-20
• Subjects: alkylation -- carbohydrates -- green chemistry -- iron -- regioselectivity; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201504477
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: In this study, [Fe(dibm)3 ] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1, 2‐ and 1, 3‐diol‐containing structures. The mechanism is proposed to proceed via a cyclic dioxolane‐type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition‐metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation. Abstract : Iron trumps tin : [Fe(dibm)3 ] (dibm= diisobutyrylmethane) has an unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1, 2‐ and 1, 3‐diols and polyols containing 1, 2‐ or 1, 3‐diols (see scheme). Alkylation leads to the same or better regioselectivities with similar or higher yields to those obtained with previous methods.