relation: http://d-scholarship-dev.library.pitt.edu/22254/
title: Tetrahydrofuran ring opening and related reactions with an N-heterocyclic carbene-boryl trifluoromethanesulfonate
creator: Solovyev, A
creator: Lacôte, E
creator: Curran, DP
description: 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. © 2013 The Royal Society of Chemistry.
date: 2013-01-01
type: Article
type: PeerReviewed
format: text/plain
language: en
rights: attached
identifier: http://d-scholarship-dev.library.pitt.edu/22254/1/licence.txt
identifier:   Solovyev, A and Lacôte, E and Curran, DP  (2013) Tetrahydrofuran ring opening and related reactions with an N-heterocyclic carbene-boryl trifluoromethanesulfonate.  Dalton Transactions, 42 (3).  695 - 700.  ISSN 1477-9226     
relation: 10.1039/c2dt31773g