One-pot synthesis of four-coordinate boron(III) complexes by the ligand-promoted organic group migration between boronic acids

Abstract Multidisciplinary applications of four-coordinate boron(III) complexes make them very attractive and challenging research field in chemistry, biology and material sciences. The dual role played by boron atom in stabilising the chelate ligand and enhancing the π-conjugation makes them very u...

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Autores principales:	Venkata S. Sadu, Hye-Rin Bin, Do-Min Lee, Kee-In Lee
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/f37e29888ba24f9ba0f6a6b65269776f
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spelling	oai:doaj.org-article:f37e29888ba24f9ba0f6a6b65269776f2021-12-02T12:32:29ZOne-pot synthesis of four-coordinate boron(III) complexes by the ligand-promoted organic group migration between boronic acids10.1038/s41598-017-00236-22045-2322https://doaj.org/article/f37e29888ba24f9ba0f6a6b65269776f2017-03-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-00236-2https://doaj.org/toc/2045-2322Abstract Multidisciplinary applications of four-coordinate boron(III) complexes make them very attractive and challenging research field in chemistry, biology and material sciences. The dual role played by boron atom in stabilising the chelate ligand and enhancing the π-conjugation makes them very useful as luminescent materials for organic electronics and photonics, and sensing and imaging probes for biomedical purposes. The conventional methods involve the use of diarylborinic acids or anhydrides and triaryl boranes, which are made from organometallic reagents. The strong nucleophilicity of these reagents limits the peripheral modifications onto the boron cores. Here, we report a metal-free one-pot synthesis of four-coordinate organoborons using boronic acids, which represents the first instance of ligand assisted organic group migration between boronic acids. A tetrahedral boron ‘ate’ complex capable of transferring an organic group to the adjacent sp2 boron within a boronic anhydride intermediate is proposed and preliminary mechanistic studies by MALDI-TOF and 11B NMR support this proposal. The products are available from a series of N,O-, N,N- and O,O-bidentate ligands upon a wide array of boronic acids. We anticipate that this reaction will impact the way of producing the four-coordinate organoborons, and propel a new discovery of such materials for optoelectronic and biomedical applications.Venkata S. SaduHye-Rin BinDo-Min LeeKee-In LeeNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-10 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Venkata S. Sadu Hye-Rin Bin Do-Min Lee Kee-In Lee One-pot synthesis of four-coordinate boron(III) complexes by the ligand-promoted organic group migration between boronic acids
description	Abstract Multidisciplinary applications of four-coordinate boron(III) complexes make them very attractive and challenging research field in chemistry, biology and material sciences. The dual role played by boron atom in stabilising the chelate ligand and enhancing the π-conjugation makes them very useful as luminescent materials for organic electronics and photonics, and sensing and imaging probes for biomedical purposes. The conventional methods involve the use of diarylborinic acids or anhydrides and triaryl boranes, which are made from organometallic reagents. The strong nucleophilicity of these reagents limits the peripheral modifications onto the boron cores. Here, we report a metal-free one-pot synthesis of four-coordinate organoborons using boronic acids, which represents the first instance of ligand assisted organic group migration between boronic acids. A tetrahedral boron ‘ate’ complex capable of transferring an organic group to the adjacent sp2 boron within a boronic anhydride intermediate is proposed and preliminary mechanistic studies by MALDI-TOF and 11B NMR support this proposal. The products are available from a series of N,O-, N,N- and O,O-bidentate ligands upon a wide array of boronic acids. We anticipate that this reaction will impact the way of producing the four-coordinate organoborons, and propel a new discovery of such materials for optoelectronic and biomedical applications.
format	article
author	Venkata S. Sadu Hye-Rin Bin Do-Min Lee Kee-In Lee
author_facet	Venkata S. Sadu Hye-Rin Bin Do-Min Lee Kee-In Lee
author_sort	Venkata S. Sadu
title	One-pot synthesis of four-coordinate boron(III) complexes by the ligand-promoted organic group migration between boronic acids
title_short	One-pot synthesis of four-coordinate boron(III) complexes by the ligand-promoted organic group migration between boronic acids
title_full	One-pot synthesis of four-coordinate boron(III) complexes by the ligand-promoted organic group migration between boronic acids
title_fullStr	One-pot synthesis of four-coordinate boron(III) complexes by the ligand-promoted organic group migration between boronic acids
title_full_unstemmed	One-pot synthesis of four-coordinate boron(III) complexes by the ligand-promoted organic group migration between boronic acids
title_sort	one-pot synthesis of four-coordinate boron(iii) complexes by the ligand-promoted organic group migration between boronic acids
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/f37e29888ba24f9ba0f6a6b65269776f
work_keys_str_mv	AT venkatassadu onepotsynthesisoffourcoordinateboroniiicomplexesbytheligandpromotedorganicgroupmigrationbetweenboronicacids AT hyerinbin onepotsynthesisoffourcoordinateboroniiicomplexesbytheligandpromotedorganicgroupmigrationbetweenboronicacids AT dominlee onepotsynthesisoffourcoordinateboroniiicomplexesbytheligandpromotedorganicgroupmigrationbetweenboronicacids AT keeinlee onepotsynthesisoffourcoordinateboroniiicomplexesbytheligandpromotedorganicgroupmigrationbetweenboronicacids
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One-pot synthesis of four-coordinate boron(III) complexes by the ligand-promoted organic group migration between boronic acids

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