Arylboronic Acids and their Myriad of Applications Beyond Organic Synthesis

Boron organometallic compounds are mainly known for their great value in organic synthesis to construct biaryls in Suzuki couplings, for arylations of olefins, for C–S, C–O, and C–N couplings or as organometallic catalysts. Herein, using arylboronic acids (Ar‐B(OH)2) as a illustrative case, we revie...

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Veröffentlicht in:European journal of organic chemistry 2020-08, Vol.2020 (31), p.4841-4877
Hauptverfasser: Hiller, Noemi de Jesus, do Amaral e Silva, Nayane Abreu, Tavares, Thais Apolinário, Faria, Robson Xavier, Eberlin, Marcos Nogueira, de Luna Martins, Daniela
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container_end_page 4877
container_issue 31
container_start_page 4841
container_title European journal of organic chemistry
container_volume 2020
creator Hiller, Noemi de Jesus
do Amaral e Silva, Nayane Abreu
Tavares, Thais Apolinário
Faria, Robson Xavier
Eberlin, Marcos Nogueira
de Luna Martins, Daniela
description Boron organometallic compounds are mainly known for their great value in organic synthesis to construct biaryls in Suzuki couplings, for arylations of olefins, for C–S, C–O, and C–N couplings or as organometallic catalysts. Herein, using arylboronic acids (Ar‐B(OH)2) as a illustrative case, we review the applications of these highly versatile molecules which expands much beyond their commonly perceived uses. Seeing primarily as “mere” intermediates in organic synthesis and organometallic catalysis, this review shows many examples of their uses in other areas of chemistry and seeks therefore to contribute to awaken scientists to the wide range of new possibilities that have been opened to boronorganic compounds, which have acted indeed as very versatile and attractive chemicals with much desirable characteristics such as safety, stability, and chemical diversity. Because the chemistry of boronic acids is extremely wide, we focused on arylboronic acids, which represent an illustrative case since their properties can be modulated by the nature of the ring or the ring substituents. Illustrative applications in analytical chemistry such as in chromatography and electrophoresis, as well as in probes to detect and quantify a variety of different chemical species and as derivatizing agents to determine enantiomeric excess in nuclear magnetic resonance spectroscopy are also given. Applications of arylboronic acids in areas as diverse as the chemistry of new materials to develop supramolecular architectures and in medical chemistry, including diagnostics, neutron capture therapy and as pharmaceutical drugs are also reviewed. Using arylboronic acids (Ar‐B(OH)2) as an illustrative case of boronorganic compounds, the applications of these highly versatile molecules which expands much beyond their commonly perceived uses are reviewed.
doi_str_mv 10.1002/ejoc.202000396
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Illustrative applications in analytical chemistry such as in chromatography and electrophoresis, as well as in probes to detect and quantify a variety of different chemical species and as derivatizing agents to determine enantiomeric excess in nuclear magnetic resonance spectroscopy are also given. Applications of arylboronic acids in areas as diverse as the chemistry of new materials to develop supramolecular architectures and in medical chemistry, including diagnostics, neutron capture therapy and as pharmaceutical drugs are also reviewed. 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Illustrative applications in analytical chemistry such as in chromatography and electrophoresis, as well as in probes to detect and quantify a variety of different chemical species and as derivatizing agents to determine enantiomeric excess in nuclear magnetic resonance spectroscopy are also given. Applications of arylboronic acids in areas as diverse as the chemistry of new materials to develop supramolecular architectures and in medical chemistry, including diagnostics, neutron capture therapy and as pharmaceutical drugs are also reviewed. 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subjects Acids
Alkenes
Analytical chemistry
Arylboronic acids
Boron compounds
Boron organometallics
Carbohydrates
Catalysis
Chemical bonds
Chemical synthesis
Chemistry
Couplings
Diols
Electrophoresis
NMR spectroscopy
Nuclear capture
Nuclear engineering
Nuclear safety
Organometallic compounds
Sensors
title Arylboronic Acids and their Myriad of Applications Beyond Organic Synthesis
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