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Article

Development of a New Methodology for Dearomative Borylation of Coumarins and Chromenes and Its Applications to Synthesize Boron-Containing Retinoids

by
Bhaskar C. Das
1,2,3,*,
Pratik Yadav
1,
Sasmita Das
1,
Mariko Saito
3 and
Todd Evans
4,*
1
Arnold and Marie Schwartz College of Pharmacy and Health Sciences, Long Island University, Brooklyn, NY 11201, USA
2
Division of Nephrology, Department of Medicine, Icahn School of Medicine at Mount Sinai, New York, NY 10029, USA
3
Nathan S. Kline Institute for Psychiatric Research, Orangeburg, NY 10962, USA
4
Department of Surgery, Weill Cornell Medical College of Cornell University, New York, NY 10065, USA
*
Authors to whom correspondence should be addressed.
Molecules 2023, 28(3), 1052; https://doi.org/10.3390/molecules28031052
Submission received: 23 December 2022 / Revised: 13 January 2023 / Accepted: 16 January 2023 / Published: 20 January 2023
(This article belongs to the Section Chemical Biology)
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Abstract

Dearomative borylation of coumarins and chromenes via conjugate addition represents a relatively unexplored and challenging task. To address this issue, herein, we report a new and general copper (I) catalyzed dearomative borylation process to synthesize boron-containing oxacycles. In this report, the borylation of coumarins, chromones, and chromenes comprising functional groups, such as esters, nitriles, carbonyls, and amides, has been achieved. In addition, the method generates different classes of potential boron-based retinoids, including the ones with oxadiazole and anthocyanin motifs. The borylated oxacycles can serve as suitable intermediates to generate a library of compounds.
Keywords: borylation; coumarins; chromenes; retinoinds; conjugate addition; oxacycles borylation; coumarins; chromenes; retinoinds; conjugate addition; oxacycles
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MDPI and ACS Style

Das, B.C.; Yadav, P.; Das, S.; Saito, M.; Evans, T. Development of a New Methodology for Dearomative Borylation of Coumarins and Chromenes and Its Applications to Synthesize Boron-Containing Retinoids. Molecules 2023, 28, 1052. https://doi.org/10.3390/molecules28031052

AMA Style

Das BC, Yadav P, Das S, Saito M, Evans T. Development of a New Methodology for Dearomative Borylation of Coumarins and Chromenes and Its Applications to Synthesize Boron-Containing Retinoids. Molecules. 2023; 28(3):1052. https://doi.org/10.3390/molecules28031052

Chicago/Turabian Style

Das, Bhaskar C., Pratik Yadav, Sasmita Das, Mariko Saito, and Todd Evans. 2023. "Development of a New Methodology for Dearomative Borylation of Coumarins and Chromenes and Its Applications to Synthesize Boron-Containing Retinoids" Molecules 28, no. 3: 1052. https://doi.org/10.3390/molecules28031052

APA Style

Das, B. C., Yadav, P., Das, S., Saito, M., & Evans, T. (2023). Development of a New Methodology for Dearomative Borylation of Coumarins and Chromenes and Its Applications to Synthesize Boron-Containing Retinoids. Molecules, 28(3), 1052. https://doi.org/10.3390/molecules28031052

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