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Issue 3, 2013
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Tetrahydrofuran ring opening and related reactions with an N-heterocyclic carbeneboryl trifluoromethanesulfonate

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Abstract

Reaction of the triflate group in dipp-Imd–BH2OTf with nucleophiles generally occurs by direct substitution to give products dipp-Imd–BH2Nu. In contrast, reaction of this boryl triflate with aryloxides (ArO) in THF resulted in insertion of THF with ring opening in between the NHC–boryl electrophile and the aryloxide to give products dipp-Imd–BH2O(CH2)4OAr. The incorporation of THF was observed with other nucleophiles such as ethylthiolate and trimethylsilanolate whose conjugate acids have pKa values similar to that of phenol. The cleavage of ethyl acetate and oxetane is reported as well. A possible mechanism is proposed.

Graphical abstract: Tetrahydrofuran ring opening and related reactions with an N-heterocyclic carbene–boryl trifluoromethanesulfonate

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Publication details

The article was received on 02 Aug 2012, accepted on 06 Sep 2012 and first published on 07 Sep 2012


Article type: Paper
DOI: 10.1039/C2DT31773G
Citation: Dalton Trans., 2013,42, 695-700
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    Tetrahydrofuran ring opening and related reactions with an N-heterocyclic carbeneboryl trifluoromethanesulfonate

    A. Solovyev, E. Lacôte and D. P. Curran, Dalton Trans., 2013, 42, 695
    DOI: 10.1039/C2DT31773G

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