Cobalt-bridged secondary building units in a titanium metal–organic framework catalyze cascade reduction of N-heteroarenes

We report here a novel Ti(3)–BPDC metal–organic framework (MOF) constructed from biphenyl-4,4′-dicarboxylate (BPDC) linkers and Ti(3)(OH)(2) secondary building units (SBUs) with permanent porosity and large 1D channels. Ti–OH groups from neighboring SBUs point toward each other with an O–O distance...

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Detalles Bibliográficos
Autores principales: Feng, Xuanyu, Song, Yang, Chen, Justin S., Li, Zhe, Chen, Emily Y., Kaufmann, Michael, Wang, Cheng, Lin, Wenbin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385530/
https://www.ncbi.nlm.nih.gov/pubmed/30881644
http://dx.doi.org/10.1039/c8sc04610g
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author Feng, Xuanyu
Song, Yang
Chen, Justin S.
Li, Zhe
Chen, Emily Y.
Kaufmann, Michael
Wang, Cheng
Lin, Wenbin
author_facet Feng, Xuanyu
Song, Yang
Chen, Justin S.
Li, Zhe
Chen, Emily Y.
Kaufmann, Michael
Wang, Cheng
Lin, Wenbin
author_sort Feng, Xuanyu
collection PubMed
description We report here a novel Ti(3)–BPDC metal–organic framework (MOF) constructed from biphenyl-4,4′-dicarboxylate (BPDC) linkers and Ti(3)(OH)(2) secondary building units (SBUs) with permanent porosity and large 1D channels. Ti–OH groups from neighboring SBUs point toward each other with an O–O distance of 2 Å, and upon deprotonation, act as the first bidentate SBU-based ligands to support Co(II)-hydride species for effective cascade reduction of N-heteroarenes (such as pyridines and quinolines) via sequential dearomative hydroboration and hydrogenation, affording piperidine and 1,2,3,4-tetrahydroquinoline derivatives with excellent activity (turnover number ∼ 1980) and chemoselectivity.
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spelling pubmed-63855302019-03-15 Cobalt-bridged secondary building units in a titanium metal–organic framework catalyze cascade reduction of N-heteroarenes Feng, Xuanyu Song, Yang Chen, Justin S. Li, Zhe Chen, Emily Y. Kaufmann, Michael Wang, Cheng Lin, Wenbin Chem Sci Chemistry We report here a novel Ti(3)–BPDC metal–organic framework (MOF) constructed from biphenyl-4,4′-dicarboxylate (BPDC) linkers and Ti(3)(OH)(2) secondary building units (SBUs) with permanent porosity and large 1D channels. Ti–OH groups from neighboring SBUs point toward each other with an O–O distance of 2 Å, and upon deprotonation, act as the first bidentate SBU-based ligands to support Co(II)-hydride species for effective cascade reduction of N-heteroarenes (such as pyridines and quinolines) via sequential dearomative hydroboration and hydrogenation, affording piperidine and 1,2,3,4-tetrahydroquinoline derivatives with excellent activity (turnover number ∼ 1980) and chemoselectivity. Royal Society of Chemistry 2018-12-19 /pmc/articles/PMC6385530/ /pubmed/30881644 http://dx.doi.org/10.1039/c8sc04610g Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Feng, Xuanyu
Song, Yang
Chen, Justin S.
Li, Zhe
Chen, Emily Y.
Kaufmann, Michael
Wang, Cheng
Lin, Wenbin
Cobalt-bridged secondary building units in a titanium metal–organic framework catalyze cascade reduction of N-heteroarenes
title Cobalt-bridged secondary building units in a titanium metal–organic framework catalyze cascade reduction of N-heteroarenes
title_full Cobalt-bridged secondary building units in a titanium metal–organic framework catalyze cascade reduction of N-heteroarenes
title_fullStr Cobalt-bridged secondary building units in a titanium metal–organic framework catalyze cascade reduction of N-heteroarenes
title_full_unstemmed Cobalt-bridged secondary building units in a titanium metal–organic framework catalyze cascade reduction of N-heteroarenes
title_short Cobalt-bridged secondary building units in a titanium metal–organic framework catalyze cascade reduction of N-heteroarenes
title_sort cobalt-bridged secondary building units in a titanium metal–organic framework catalyze cascade reduction of n-heteroarenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385530/
https://www.ncbi.nlm.nih.gov/pubmed/30881644
http://dx.doi.org/10.1039/c8sc04610g
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