One-Pot Reductive Amination and Suzuki–Miyaura Cross-Coupling of Formyl Aryl and Heteroaryl MIDA Boronates in Array Format

Grob, Jonathan E.; Nunez, Jill; Dechantsreiter, Michael A.; Hamann, Lawrence G.

doi:10.1021/jo2005928

Cited by 34 publications

(14 citation statements)

References 20 publications

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“…We also note an acceptable 44% yield for the somewhat elusive benzaldehyde derivative 2q. 23 Having considerably improved upon conventional reaction times for MIDA boronate synthesis using microwave chemistry, our next iteration needed to address the issues of solvent suitability. PEG 300 was considered as a worthy candidate solvent as it has similar properties to DMSO, in terms of polarity and hydrogen bond acceptor properties, as highlighted by Jessop, in two Kamlet-Taft plots of common solvents.…”

Section: Introductionmentioning

confidence: 99%

Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

Kemmitt

Emmerson

et al. 2014

Tetrahedron

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(2014) Microwavemediated synthesis of N-methyliminodiacetic acid (MIDA) boronates. Tetrahedron, 70 (47). pp. [9125][9126][9127][9128][9129][9130][9131] This version is available from Sussex Research Online: http://sro.sussex.ac.uk/53847/ This document is made available in accordance with publisher policies and may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the URL above for details on accessing the published version. Copyright and reuse:Sussex Research Online is a digital repository of the research output of the University.Copyright and all moral rights to the version of the paper presented here belong to the individual author(s) and/or other copyright owners. To the extent reasonable and practicable, the material made available in SRO has been checked for eligibility before being made available.Copies of full text items generally can be reproduced, displayed or performed and given to third parties in any format or medium for personal research or study, educational, or not-for-profit purposes without prior permission or charge, provided that the authors, title and full bibliographic details are credited, a hyperlink and/or URL is given for the original metadata page and the content is not changed in any way. ABSTRACT: A library of over twenty, mainly aryl or heteroaryl, N-methyliminodiacetic acid (MIDA) boronates has been synthesized. A rapid microwave-mediated (MW) method (5-10 mins) has been developed using polyethylene glycol 300 (PEG 300) as solvent. However, acetonitrile (MeCN) and dimethylformamide (DMF) were found to be alternative solvents, the latter especially for 2-substituted aryl boronic acids.

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Section: Introductionmentioning

confidence: 99%

Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

Kemmitt

Emmerson

et al. 2014

Tetrahedron

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“…One‐pot synthesis of stilbenes by dehydrohalogenation–Heck olefination and multi‐component Wittig–Heck reaction was recently accomplished by the present authors d. Cascade reactions involving Suzuki reaction as one of the steps have been reported in the literature, although almost all involve phosphine‐based catalyst systems [2e,36–50]. A few examples of double Suzuki reactions have been reported in which excellent control for two different reagents was achieved .…”

Section: Resultsmentioning

confidence: 97%

1‐(α‐Aminobenzyl)‐2‐naphthol as phosphine‐free ligand for Pd‐catalyzed Suzuki and one‐pot Wittig‐Suzuki reaction

Chaudhary

Bedekar

2012

Applied Organom Chemis

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Air stable and easily accessible, 1-(a-aminobenzyl)-2-naphthols are used as efficient phosphine-free ligands in palladiumcatalyzed Suzuki reaction for a variety of substrates under conventional heating as well as ultrasonic conditions. Multibrominated aromatic substrates were successfully converted to corresponding arylated moieties with good conversion and selectivity. A novel one-pot two-step cascade reaction strategy involving Wittig and Suzuki reactions is developed for efficient synthesis of 4-styryl biphenyls (C 6 -C 2 -C 6 -C 6 unit).

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“…The MIDA boronate, obtained from boronic acid [42,43], was also synthesized as an alternative boron reagent for the modification of the BODIPY core. MIDA boronate ester is stable under various conditions and can slowly release the corresponding boronic acid in mild basic aqueous solution [42].…”

Section: Resultsmentioning

confidence: 99%

A Straightforward Substitution Strategy to Tune BODIPY Dyes Spanning the Near-Infrared Region via Suzuki–Miyaura Cross-Coupling

Otsuka

Matsumiya

et al. 2018

Materials

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In this study, a series of new red and near-infrared (NIR) dyes derived from 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) were developed by introducing thiophene and its derivatives to the 3- and 5- positions of the dichloroBODIPY core. For the first time, cyclictriol boronates and N-methyliminodiacetic acid (MIDA) boronate were used as organoboron species to couple with 3,5-dichloroBODIPY via the one-step Suzuki–Miyaura cross-coupling. Six kinds of thieno-expended BODIPY dyes were synthesized in acceptable yields ranging from 31% to 79%. All six dyes showed different absorption and emission wavelengths spanning a wide range (c.a. 600–850 nm) in the red and NIR regions with relatively high quantum yields (19–85%). Cellular imaging of 8-(2,6-dimethylphenyl)-re3,5-di(2-thienyl)-BODIPY (dye 1) was conducted using bovine cumulus cells, and the fluorescence microscopy images indicated that the chromophore efficiently accumulated and was exclusively localized in the cytoplasm, suggesting it could be utilized as a subcellular probe. All six dyes were characterized using 1H-NMR and mass spectrometry.

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One-Pot Reductive Amination and Suzuki–Miyaura Cross-Coupling of Formyl Aryl and Heteroaryl MIDA Boronates in Array Format

Cited by 34 publications

References 20 publications

Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

Microwave-mediated synthesis of N-methyliminodiacetic acid (MIDA) boronates

1‐(α‐Aminobenzyl)‐2‐naphthol as phosphine‐free ligand for Pd‐catalyzed Suzuki and one‐pot Wittig‐Suzuki reaction

A Straightforward Substitution Strategy to Tune BODIPY Dyes Spanning the Near-Infrared Region via Suzuki–Miyaura Cross-Coupling

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