Cobalt‐Catalyzed Redox‐Neutral Sulfonylative Coupling from (Hetero)aryl Boronic Acids, Ammonium Salts and Potassium Metabisulfite

Herein, we give a full account of the development of the palladium-catalysed cross-coupling of benzylammonium salts with boronic acids. A range of benzylamine-derived quaternary ammonium salts can be coupled with boronic acids under relatively mild conditions. Our optimization has identified ligands that can be used to chemoselectively cross-couple at the ammonium in the presence of chlorides. We demonstrate that intramolecular palladium-catalysed C–H activation is also a viable pathway for the putative benzyl-Pd(II) intermediate obtained upon oxidative addition and have optimised this to obtain fluorene in good yield.

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Efficient N -heterocyclic carbene nickel pincer complexes catalyzed cross coupling of benzylic ammonium salts with boronic acids

Chinese Chemical Letters ◽

10.1016/j.cclet.2016.09.006 ◽

2017 ◽

Vol 28 (2) ◽

pp. 350-353 ◽

Cited By ~ 8

Author(s):

Xi-Yu Liu ◽

Hai-Bo Zhu ◽

Ya-Jing Shen ◽

Jian Jiang ◽

Tao Tu

Keyword(s):

Cross Coupling ◽

Boronic Acids ◽

Ammonium Salts ◽

Pincer Complexes

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ChemInform Abstract: Nickel-Catalyzed Cross Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C-N Bond Activation.

ChemInform ◽

10.1002/chin.201324065 ◽

2013 ◽

Vol 44 (24) ◽

pp. no-no

Author(s):

Prantik Maity ◽

Danielle M. Shacklady-McAtee ◽

Glenn P. A. Yap ◽

Eric R. Sirianni ◽

Mary P. Watson

Keyword(s):

Bond Activation ◽

Boronic Acids ◽

Ammonium Salts

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Nickel-Catalyzed Cross Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C–N Bond Activation

Journal of the American Chemical Society ◽

10.1021/ja3089422 ◽

2012 ◽

Vol 135 (1) ◽

pp. 280-285 ◽

Cited By ~ 174

Author(s):

Prantik Maity ◽

Danielle M. Shacklady-McAtee ◽

Glenn P. A. Yap ◽

Eric R. Sirianni ◽

Mary P. Watson

Keyword(s):

Bond Activation ◽

Boronic Acids ◽

Ammonium Salts

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A Mild and Simple Method for Making MIDA Boronates

10.26434/chemrxiv.12054036.v1 ◽

2020 ◽

Author(s):

Aidan Kelly ◽

Peng-Jui (Ruby) Chen ◽

Jenna Klubnick ◽

Daniel J. Blair ◽

Martin D. Burke

Keyword(s):

Organic Synthesis ◽

Boronic Acids ◽

Simple Method ◽

Direct Preparation ◽

Synthesis Procedure ◽

Harsh Conditions

<div> <div> <div> <p>Existing methods for making MIDA boronates require harsh conditions and complex procedures to achieve dehydration. Here we disclose that a pre-dried form of MIDA, MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in labs that do not specialize in organic synthesis. </p> </div> </div> </div>

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Access to Fe(II) Bis(σ-B-H) Aminoborane Complexes via Protonation of a Borohydride Complex and Dehydrogenation of Amine-Boranes

10.26434/chemrxiv.8063120.v1 ◽

2019 ◽

Author(s):

Nikolaus Gorgas ◽

Berthold Stöger ◽

Luis F. Veiros ◽

Karl Kirchner

Keyword(s):

Structural Characterization ◽

Ammonium Salts ◽

Iron Based ◽

Amine Boranes

We report on the first synthesis and structural characterization of the iron based aminoborane complexes. These species are formed upon protonation of a borohydride complex by ammonium salts.<br>

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