Functionalization at Will of Rim-Differentiated Pillar[5]arenes

[Image: see text] The development of an efficient synthetic route toward rim-differentiated C(5)-symmetric pillar[5]arenes (P[5]s), whose two rims are decorated with different chemical functionalities, opens up successive transformations of this macrocyclic scaffold. This paper describes a gram-scal...

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Autores principales: Demay-Drouhard, Paul, Du, Ke, Samanta, Kushal, Wan, Xintong, Yang, Weiwei, Srinivasan, Rajavel, Sue, Andrew C.-H., Zuilhof, Han
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6558637/
https://www.ncbi.nlm.nih.gov/pubmed/31002251
http://dx.doi.org/10.1021/acs.orglett.9b01123
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author Demay-Drouhard, Paul
Du, Ke
Samanta, Kushal
Wan, Xintong
Yang, Weiwei
Srinivasan, Rajavel
Sue, Andrew C.-H.
Zuilhof, Han
author_facet Demay-Drouhard, Paul
Du, Ke
Samanta, Kushal
Wan, Xintong
Yang, Weiwei
Srinivasan, Rajavel
Sue, Andrew C.-H.
Zuilhof, Han
author_sort Demay-Drouhard, Paul
collection PubMed
description [Image: see text] The development of an efficient synthetic route toward rim-differentiated C(5)-symmetric pillar[5]arenes (P[5]s), whose two rims are decorated with different chemical functionalities, opens up successive transformations of this macrocyclic scaffold. This paper describes a gram-scale synthesis of a C(5)-symmetric penta-hydroxy P[5] precursor, and a range of highly efficient reactions that allow functionalizing either rim at will via, e.g., sulfur(VI) fluoride exchange (SuFEx) reactions, esterifications, or Suzuki–Miyaura coupling. Afterward, BBr(3) demethylation activates another rim for similar functionalizations.
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spelling pubmed-65586372019-06-12 Functionalization at Will of Rim-Differentiated Pillar[5]arenes Demay-Drouhard, Paul Du, Ke Samanta, Kushal Wan, Xintong Yang, Weiwei Srinivasan, Rajavel Sue, Andrew C.-H. Zuilhof, Han Org Lett [Image: see text] The development of an efficient synthetic route toward rim-differentiated C(5)-symmetric pillar[5]arenes (P[5]s), whose two rims are decorated with different chemical functionalities, opens up successive transformations of this macrocyclic scaffold. This paper describes a gram-scale synthesis of a C(5)-symmetric penta-hydroxy P[5] precursor, and a range of highly efficient reactions that allow functionalizing either rim at will via, e.g., sulfur(VI) fluoride exchange (SuFEx) reactions, esterifications, or Suzuki–Miyaura coupling. Afterward, BBr(3) demethylation activates another rim for similar functionalizations. American Chemical Society 2019-04-19 2019-06-07 /pmc/articles/PMC6558637/ /pubmed/31002251 http://dx.doi.org/10.1021/acs.orglett.9b01123 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Demay-Drouhard, Paul
Du, Ke
Samanta, Kushal
Wan, Xintong
Yang, Weiwei
Srinivasan, Rajavel
Sue, Andrew C.-H.
Zuilhof, Han
Functionalization at Will of Rim-Differentiated Pillar[5]arenes
title Functionalization at Will of Rim-Differentiated Pillar[5]arenes
title_full Functionalization at Will of Rim-Differentiated Pillar[5]arenes
title_fullStr Functionalization at Will of Rim-Differentiated Pillar[5]arenes
title_full_unstemmed Functionalization at Will of Rim-Differentiated Pillar[5]arenes
title_short Functionalization at Will of Rim-Differentiated Pillar[5]arenes
title_sort functionalization at will of rim-differentiated pillar[5]arenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6558637/
https://www.ncbi.nlm.nih.gov/pubmed/31002251
http://dx.doi.org/10.1021/acs.orglett.9b01123
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