Organoboron compounds are very important derivatives because of their profound impacts on medicinal, biological as well as industrial applications. The development of several novel borylation methodologies has achieved momentous interest among synthetic chemists. In this scenario, eco-friendly light-induced borylation is progressively becoming one of the best synthetic tools in recent days to prepare organoboronic ester and acid derivatives based on green chemistry rules. In this article, we have discussed all the UV- and visible-light-induced borylation strategies developed in the last decade. Furthermore, special attention is given to the mechanisms of these borylation methodologies for better understanding of reaction insights.
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http://dx.doi.org/10.1039/d1ob00323b | DOI Listing |
J Am Chem Soc
November 2024
School of Pharmacy, Fudan University, Shanghai, China, 201203.
Norzoanthamine is a structurally complex polycyclic natural product that expresses a broad range of biological activities, rendering facile access to it and its analogs of considerable importance in drug discovery and development. However, strategies for efficient access to this class of marine alkaloids remain lacking. Here, we report a strategy, characterized by three key photochemical reactions, that we used to synthesize norzoanthamine in 16 steps.
View Article and Find Full Text PDFChem Sci
August 2024
Flow Chemistry Group, Van 't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam Science Park 904 1098 XH Amsterdam The Netherlands
Photoinduced halogen-atom transfer (XAT) has rapidly emerged as a programmable approach to generate carbon-centered radical intermediates, mainly relying on silyl and α-aminoalkyl radicals as halogen abstractors. More recently, ligated boryl radicals have also been proposed as effective halogen abstractors under visible-light irradiation. In this study, we describe the use of this approach to enable C(sp)-C(sp) bond formation radical addition of carbon-centered radicals generated XAT onto chloroalkynes.
View Article and Find Full Text PDFOrg Biomol Chem
April 2024
School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan 430070, P. R. China.
An efficient method was developed for the one-pot construction of C-B and C-I visible light-induced transformation of nitroarenes. This protocol relies on the photochemical properties of nitroarenes under visible light, followed by reduction with Bpin and diazotization with BuONO. An array of arylboronates and iodobenzenes were constructed smoothly after excitation with purple LEDs at room temperature.
View Article and Find Full Text PDFJ Org Chem
April 2024
Henan Key Laboratory of Boron Chemistry and Advanced Energy Materials, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
A green and practical protocol of defluoroborylation of polyfluoroarenes with stable and readily accessible NHC-borane was developed, using 1,2-diphenyldisulfane as a hydrogen atom transfer (HAT) and single electron transfer (SET) reagent precursor under visible-light irradiation, leading to the concise formation of value-added fluorinated organoboron scaffolds. Mechanism studies revealed the method underwent a boryl radical addition reaction with polyfluoroarene, followed by successive single electron transfer pathways and defluorination of the C-F bond to offer the targeted product. This unprecedented platform relies on 1,2-diphenyldisulfane and base without using expensive photocatalysts, highlighting the methodology has promising application value to prepare borylated polyfluoroarene compounds.
View Article and Find Full Text PDFOrg Lett
March 2024
Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8550, Japan.
We have developed visible-light-induced -hydroboration of diaryl alkynes via direct photoexcitation of in-situ-generated diboron complexes, affording previously elusive ()-1,2-diaryl-vinylboronates with high stereoselectivity. Experimental, spectroscopic, and theoretical mechanistic studies revealed that the triplet-state borate complex facilitates B-B bond cleavage and the desired C-B bond formation. This methodology does not require any catalyst and is operationally simple.
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