A Strategy to Control the Reactivation of Frustrated Lewis Pairs from Shelf-Stable Carbene Borane Complexes

N-Phosphine oxide substituted imidazolylidenes (PoxIms) have been synthesized and fully characterized. These species can undergo significant changes to the spatial environment surrounding their carbene center through rotation of the phosphine oxide moiety. Either classical Lewis adducts (CLAs) or fr...

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Autores principales: Hoshimoto, Yoichi, Kinoshita, Takuya, Ohashi, Masato, Ogoshi, Sensuke
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4600235/
https://www.ncbi.nlm.nih.gov/pubmed/26315680
http://dx.doi.org/10.1002/anie.201505974
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author Hoshimoto, Yoichi
Kinoshita, Takuya
Ohashi, Masato
Ogoshi, Sensuke
author_facet Hoshimoto, Yoichi
Kinoshita, Takuya
Ohashi, Masato
Ogoshi, Sensuke
author_sort Hoshimoto, Yoichi
collection PubMed
description N-Phosphine oxide substituted imidazolylidenes (PoxIms) have been synthesized and fully characterized. These species can undergo significant changes to the spatial environment surrounding their carbene center through rotation of the phosphine oxide moiety. Either classical Lewis adducts (CLAs) or frustrated Lewis pairs (FLPs) are thus formed with B(C(6)F(5))(3) depending on the orientation of the phosphine oxide group. A strategy to reactivate FLPs from CLAs by exploiting molecular motions that are responsive to external stimuli has therefore been developed. The reactivation conditions were successfully controlled by tuning the strain in the PoxIm–B(C(6)F(5))(3) complexes so that reactivation only occurred above ambient temperature.
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spelling pubmed-46002352015-10-14 A Strategy to Control the Reactivation of Frustrated Lewis Pairs from Shelf-Stable Carbene Borane Complexes Hoshimoto, Yoichi Kinoshita, Takuya Ohashi, Masato Ogoshi, Sensuke Angew Chem Int Ed Engl Communications N-Phosphine oxide substituted imidazolylidenes (PoxIms) have been synthesized and fully characterized. These species can undergo significant changes to the spatial environment surrounding their carbene center through rotation of the phosphine oxide moiety. Either classical Lewis adducts (CLAs) or frustrated Lewis pairs (FLPs) are thus formed with B(C(6)F(5))(3) depending on the orientation of the phosphine oxide group. A strategy to reactivate FLPs from CLAs by exploiting molecular motions that are responsive to external stimuli has therefore been developed. The reactivation conditions were successfully controlled by tuning the strain in the PoxIm–B(C(6)F(5))(3) complexes so that reactivation only occurred above ambient temperature. WILEY-VCH Verlag 2015-09-28 2015-08-06 /pmc/articles/PMC4600235/ /pubmed/26315680 http://dx.doi.org/10.1002/anie.201505974 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. https://creativecommons.org/licenses/by-nc-nd/4.0/ © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
spellingShingle Communications
Hoshimoto, Yoichi
Kinoshita, Takuya
Ohashi, Masato
Ogoshi, Sensuke
A Strategy to Control the Reactivation of Frustrated Lewis Pairs from Shelf-Stable Carbene Borane Complexes
title A Strategy to Control the Reactivation of Frustrated Lewis Pairs from Shelf-Stable Carbene Borane Complexes
title_full A Strategy to Control the Reactivation of Frustrated Lewis Pairs from Shelf-Stable Carbene Borane Complexes
title_fullStr A Strategy to Control the Reactivation of Frustrated Lewis Pairs from Shelf-Stable Carbene Borane Complexes
title_full_unstemmed A Strategy to Control the Reactivation of Frustrated Lewis Pairs from Shelf-Stable Carbene Borane Complexes
title_short A Strategy to Control the Reactivation of Frustrated Lewis Pairs from Shelf-Stable Carbene Borane Complexes
title_sort strategy to control the reactivation of frustrated lewis pairs from shelf-stable carbene borane complexes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4600235/
https://www.ncbi.nlm.nih.gov/pubmed/26315680
http://dx.doi.org/10.1002/anie.201505974
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