An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols |
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Authors: | Bo Ren Prof Olof Ramström Qiang Zhang Jiantao Ge Prof Hai Dong |
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Institution: | 1. Key laboratory of Material Chemistry for, Energy Conversion and Storage, Ministry of Education, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, P.R. China;2. Department of Chemistry, KTH-Royal Institute of Technology, Stockholm, Sweden;3. (+86)?27‐87793242 |
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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. |
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Keywords: | alkylation carbohydrates green chemistry iron regioselectivity |
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