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Issue 3, 2013
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Tetrahydrofuran ring opening and related reactions with an N-heterocyclic carbene–boryl 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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Article information


Submitted
02 Aug 2012
Accepted
06 Sep 2012
First published
07 Sep 2012

Dalton Trans., 2013,42, 695-700
Article type
Paper

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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