eprintid: 22254
rev_number: 24
userid: 1418
dir: disk0/00/02/22/54
datestamp: 2014-07-18 21:16:45
lastmod: 2021-06-12 22:56:28
status_changed: 2014-07-18 21:16:45
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Solovyev, A
creators_name: Lacôte, E
creators_name: Curran, DP
creators_email: 
creators_email: 
creators_email: curran@pitt.edu
creators_id: 
creators_id: 
creators_id: CURRAN
title: Tetrahydrofuran ring opening and related reactions with an N-heterocyclic carbene-boryl trifluoromethanesulfonate
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
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. © 2013 The Royal Society of Chemistry.
date: 2013-01-01
date_type: published
publication: Dalton Transactions
volume: 42
number: 3
pagerange: 695 - 700
refereed: TRUE
issn: 1477-9226
id_number: 10.1039/c2dt31773g
pmid: 23001364
citation:   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     
document_url: http://d-scholarship-dev.library.pitt.edu/22254/1/licence.txt