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Tetrahydrofuran ring opening and related reactions with an N-heterocyclic carbene-boryl trifluoromethanesulfonate

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

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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. © 2013 The Royal Society of Chemistry.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Solovyev, A
Lacôte, E
Curran, DPcurran@pitt.eduCURRAN
Date: 1 January 2013
Date Type: Publication
Journal or Publication Title: Dalton Transactions
Volume: 42
Number: 3
Page Range: 695 - 700
DOI or Unique Handle: 10.1039/c2dt31773g
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1477-9226
PubMed ID: 23001364
Date Deposited: 18 Jul 2014 21:16
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/22254

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