MIDA boronates are among the most useful reagents for the Suzuki-Miyaura reaction. This chemistry typically generates new bonds between two aromatic rings, thereby restricting access to important areas of chemical space. Here we demonstrate the coupling of MIDA boronates to allylic electrophiles, including a new synthesis of the well-known COX inhibitor ibuprofen.
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| http://dx.doi.org/10.1039/d0ra03338c | DOI Listing |
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Chemoselective Deprotection of Symmetrically Diprotected Resorcinol -Methyliminodiacetate (MIDA) Boronates Using the MIDA Boronate Moiety as a Blocking Group: Synthesis of Monoprotected Resorcinol MIDA Boronates.
Org Lett
December 2024
Department of Chemistry, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul 02841, Republic of Korea.
A novel protocol for the synthesis of monoprotected resorcinol -methyliminodiacetate (MIDA) boronates was developed via the chemoselective deprotection of diprotected resorcinol MIDA derivatives with identical protecting groups, utilizing the MIDA boronate moiety as a blocking group for deprotection. This protocol exhibited a broad substrate scope, and the resulting MIDA boronates were readily isolated by simple filtration from the reaction mixture. Furthermore, the utility of this protocol was demonstrated by converting the resulting MIDA boronates into value-added chemicals containing resorcinol scaffolds.
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J Am Chem Soc
July 2024
State Key Laboratory of Structural Chemistry, and Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou 350100, China.
Developing a general, highly efficient, and enantioselective catalytic method for the synthesis of chiral alcohols is still a formidable challenge. We report in this article the asymmetric transfer hydrogenation (ATH) of -methyliminodiacetyl (MIDA) acylboronates as a general substrate-independent entry to enantioenriched secondary alcohols. ATH of acyl-MIDA-boronates with (het)aryl, alkyl, alkynyl, alkenyl, and carbonyl substituents delivers a variety of enantioenriched α-boryl alcohols.
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Dalton Trans
June 2024
Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
Article Synopsis
- Vinylidene rearrangement of alkynes is a powerful method for transforming alkynes, but the application of borylalkynes in this process has not been extensively studied.
- This research explores the rearrangement of internal borylalkynes using a cationic ruthenium complex, highlighting that the reaction is effective for both tri- and tetracoordinate boryl groups, with reaction rates significantly influenced by the Lewis acidity of the boryl group.
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The discovery of a new class of heteroatom-rich boron-containing molecules (BCMs) and iterative cross-coupling (ICC) partners created a toolbox for future drug developments using organoboron compounds. Herein, we report the potential utility of 1,3-enyne MIDA boronates to access diverse -difluoro MIDA boronates novel 1,2-alkyne shift. This unique reactivity of 1,3-enyne MIDA boronates offers facile access to previously challenging β-difluorinated alkyl borons.
View Article and Find Full Text PDFNHC-Au-Catalyzed Isomerization of Propargylic B(MIDA)s to Allenes and Double Isomerization of Alkynes to 1,3-Dienes.
Adv Sci (Weinh)
June 2024
Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou, 510006, China.
The synthesis of allenyl boronates is an important yet challenging topic in organic synthesis. Reported herein is an NHC-gold-catalyzed 1,3-H shift toward allenyl boronates synthesis from simple propargylic B(MIDA)s. Mechanistic studies suggest dual roles of the boryl moiety in the reaction: to activate the substrate for isomerization and at the same time, to prevent the allene product from further isomerization.
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