Contrasting Frustrated Lewis Pair Reactivity with Selenium‐ and Boron‐Based Lewis Acids

Contrasting Frustrated Lewis Pair Reactivity with Selenium‐ and Boron‐Based Lewis Acids

The activation of π‐bonds in diynyl esters has been investigated by using soft and hard Lewis acids. In the case of the soft selenium Lewis acid PhSeCl, sequential activation of the alkyne bonds leads initially to an isocoumarin (1 equiv PhSeCl) and then to a tetracyclic conjugated structure with th...

Full description

Bibliographic Details
Main Authors: Wilkins, Lewis C., Günther, Benjamin A. R., Walther, Melanie, Lawson, James R., Wirth, Thomas, Melen, Rebecca L.
Format: Online
Language:English
Published: John Wiley and Sons Inc. 2016
Online Access:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5113806/
id pubmed-5113806
recordtype oai_dc
spelling pubmed-51138062016-12-02 Contrasting Frustrated Lewis Pair Reactivity with Selenium‐ and Boron‐Based Lewis Acids Wilkins, Lewis C. Günther, Benjamin A. R. Walther, Melanie Lawson, James R. Wirth, Thomas Melen, Rebecca L. Communications The activation of π‐bonds in diynyl esters has been investigated by using soft and hard Lewis acids. In the case of the soft selenium Lewis acid PhSeCl, sequential activation of the alkyne bonds leads initially to an isocoumarin (1 equiv PhSeCl) and then to a tetracyclic conjugated structure with the isocoumarin subunit fused to a benzoselenopyran (3 equiv PhSeCl). Conversely, the reaction with the hard Lewis acidic borane B(C6F5)3 initiates a cascade reaction to yield a complex π‐conjugated system containing phthalide and indene subunits. John Wiley and Sons Inc. 2016-08-03 2016-09-05 /pmc/articles/PMC5113806/ /pubmed/27484052 http://dx.doi.org/10.1002/anie.201605239 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
repository_type Open Access Journal
institution_category Foreign Institution
institution US National Center for Biotechnology Information
building NCBI PubMed
collection Online Access
language English
format Online
author Wilkins, Lewis C.
Günther, Benjamin A. R.
Walther, Melanie
Lawson, James R.
Wirth, Thomas
Melen, Rebecca L.
spellingShingle Wilkins, Lewis C.
Günther, Benjamin A. R.
Walther, Melanie
Lawson, James R.
Wirth, Thomas
Melen, Rebecca L.
Contrasting Frustrated Lewis Pair Reactivity with Selenium‐ and Boron‐Based Lewis Acids
author_facet Wilkins, Lewis C.
Günther, Benjamin A. R.
Walther, Melanie
Lawson, James R.
Wirth, Thomas
Melen, Rebecca L.
author_sort Wilkins, Lewis C.
title Contrasting Frustrated Lewis Pair Reactivity with Selenium‐ and Boron‐Based Lewis Acids
title_short Contrasting Frustrated Lewis Pair Reactivity with Selenium‐ and Boron‐Based Lewis Acids
title_full Contrasting Frustrated Lewis Pair Reactivity with Selenium‐ and Boron‐Based Lewis Acids
title_fullStr Contrasting Frustrated Lewis Pair Reactivity with Selenium‐ and Boron‐Based Lewis Acids
title_full_unstemmed Contrasting Frustrated Lewis Pair Reactivity with Selenium‐ and Boron‐Based Lewis Acids
title_sort contrasting frustrated lewis pair reactivity with selenium‐ and boron‐based lewis acids
description The activation of π‐bonds in diynyl esters has been investigated by using soft and hard Lewis acids. In the case of the soft selenium Lewis acid PhSeCl, sequential activation of the alkyne bonds leads initially to an isocoumarin (1 equiv PhSeCl) and then to a tetracyclic conjugated structure with the isocoumarin subunit fused to a benzoselenopyran (3 equiv PhSeCl). Conversely, the reaction with the hard Lewis acidic borane B(C6F5)3 initiates a cascade reaction to yield a complex π‐conjugated system containing phthalide and indene subunits.
publisher John Wiley and Sons Inc.
publishDate 2016
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5113806/
_version_ 1613731434449600512

Similar Items