scholarly journals Acylboronates in Polarity-Reversed Generation of Acyl Palladium(II) Intermediates

2021 ◽  
Author(s):  
Alina Trofimova ◽  
Aleksandra Holownia ◽  
chieh-hung tien ◽  
martynas sirvinskas ◽  
Andrei Yudin
Keyword(s):  
Mass Spectrometry ◽  
Cross Coupling ◽  
Polarity Reversal ◽  
Coupling Process ◽  
Broad Scope ◽  
Acyl Anion ◽  
Pseudo Halides

We report a catalytic cross-coupling process between aryl (pseudo)halides and boron-based acyl anion equivalents. This mode of acylboronate reactivity represents polarity reversal, which is supported by the observation of tetracoordinated boronate and acyl palladium(II) species by <sup>11</sup>B, <sup>31</sup>P NMR, and mass spectrometry. A broad scope of aliphatic and aromatic acylboronates has been examined, as well as a variety of aryl (pseudo)halides.

scholarly journals Acylboronates in Polarity-Reversed Generation of Acyl Palladium(II) Intermediates

2021 ◽  
Author(s):  
Alina Trofimova ◽  
Aleksandra Holownia ◽  
chieh-hung tien ◽  
martynas sirvinskas ◽  
Andrei Yudin
Keyword(s):  
Mass Spectrometry ◽  
Cross Coupling ◽  
Polarity Reversal ◽  
Coupling Process ◽  
Broad Scope ◽  
Acyl Anion ◽  
Pseudo Halides

We report a catalytic cross-coupling process between aryl (pseudo)halides and boron-based acyl anion equivalents. This mode of acylboronate reactivity represents polarity reversal, which is supported by the observation of tetracoordinated boronate and acyl palladium(II) species by <sup>11</sup>B, <sup>31</sup>P NMR, and mass spectrometry. A broad scope of aliphatic and aromatic acylboronates has been examined, as well as a variety of aryl (pseudo)halides.

Suzuki–Miyaura cross-coupling for chemoproteomic applications

2020 ◽  
Author(s):  
Jian Cao ◽  
Ernest Armenta ◽  
Lisa Boatner ◽  
Heta Desai ◽  
Neil Chan ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Cross Coupling ◽  
Protein Profiling ◽  
Protein Labeling ◽  
Caspase 8 ◽  
Complex Cell ◽  
Bioorthogonal Chemistry ◽  
Reaction Conditions ◽  
Target Deconvolution ◽  
Palladium Catalyzed

Bioorthogonal chemistry is a mainstay of chemoproteomic sample preparation workflows. While numerous transformations are now available, chemoproteomic studies still rely overwhelmingly on copper-catalyzed azide –alkyne cycloaddition (CuAAC) or 'click' chemistry. Here we demonstrate that gel-based activity-based protein profiling (ABPP) and mass-spectrometry-based chemoproteomic profiling can be conducted using Suzuki–Miyaura cross-coupling. We identify reaction conditions that proceed in complex cell lysates and find that Suzuki –Miyaura cross-coupling and CuAAC yield comparable chemoproteomic coverage. Importantly, Suzuki–Miyaura is also compatible with chemoproteomic target deconvolution, as demonstrated using structurally matched probes tailored to react with the cysteine protease caspase-8. Uniquely enabled by the observed orthogonality of palladium-catalyzed cross-coupling and CuAAC, we combine both reactions to achieve dual protein labeling.

Metal-Free Hydrogen Evolution Cross-Coupling Enabled by Synergistic Photoredox and Polarity Reversal Catalysis

2021 ◽  
Author(s):  
Jilei Cao ◽  
Xiaona Yang ◽  
Lishuang Ma ◽  
Kanghui Lu ◽  
Rong Zhou
Keyword(s):  
Hydrogen Evolution ◽  
Cross Coupling ◽  
Polarity Reversal ◽  
Metal Free ◽  
Free Hydrogen ◽  
Synergistic Combination

A synergistic combination of photoredox and polarity reversal catalysis enabled a hydrogen evolution cross-coupling of silanes with H2O, alcohols, phenols, and silanols, which afforded the corresponding silanols, monosilyl ethers, and...

ChemInform Abstract: The Preparation of Substituted Pyrazoles from β,β-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process.

ChemInform ◽  
2010 ◽  
Vol 41 (27) ◽  
pp. no-no
Author(s):  
Sandra Beltran-Rodil ◽  
Michael G. Edwards ◽  
David S. Pugh ◽  
Mark Reid ◽  
Richard J. K. Taylor
Keyword(s):  
Cross Coupling ◽  
Coupling Process ◽  
Substituted Pyrazoles

scholarly journals Synthesis of Pd Complexes Containing Tailed NHC Ligands and Their Use in a Semicontinuous Membrane-Assisted Suzuki Cross-Coupling Process

2018 ◽  
Vol 22 (11) ◽  
pp. 1509-1517 ◽  
Author(s):  
Dominic Ormerod ◽  
Matthieu Dorbec ◽  
Eugen Merkul ◽  
Nadya Kaval ◽  
Nicolas Lefèvre ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Process ◽  
Pd Complexes

KI-Promoted Oxidative Coupling of Styrenes with Indoles under Metal-Free Conditions: Facile Access to C-3 Dicarbonyl Indoles

Synthesis ◽  
2019 ◽  
Vol 51 (18) ◽  
pp. 3511-3519
Author(s):  
Bochao Zhou ◽  
Shiyu Guo ◽  
Zheng Fang ◽  
Zhao Yang ◽  
Chengkou Liu ◽  
...  
Keyword(s):  
Efficient Method ◽  
Oxidative Coupling ◽  
Isotope Labeling ◽  
Cross Coupling ◽  
Metal Free ◽  
Broad Scope ◽  
Plausible Mechanism ◽  
Isotope Labeling Experiments

A new and efficient method for the synthesis of C-3 dicarbonyl indoles via oxidative cross-coupling of styrenes with indoles under metal-free conditions has been developed. Moreover, a broad scope of C-3 dicarbonyl indoles in moderate to good yields were obtained, and a plausible mechanism is proposed based on control and isotope-labeling experiments.

scholarly journals A Robust Pd-Catalyzed C–S Cross-Coupling Process Enabled by Ball-Milling

2020 ◽  
Vol 22 (19) ◽  
pp. 7433-7438
Author(s):  
Andrew C. Jones ◽  
William I. Nicholson ◽  
Harry R. Smallman ◽  
Duncan L. Browne
Keyword(s):  
Ball Milling ◽  
Cross Coupling ◽  
Coupling Process

scholarly journals General Approach to the Total Synthesis of Macroline-Related Sarpagine and Ajmaline Alkaloids1

2008 ◽  
Vol 3 (11) ◽  
pp. 1934578X0800301
Author(s):  
Chitra R. Edwankar ◽  
Rahul V. Edwankar ◽  
Sundari Rallapalli ◽  
James M. Cook
Keyword(s):  
Total Synthesis ◽  
Cross Coupling ◽  
Complex Molecules ◽  
Coupling Process ◽  
Efficient Strategy ◽  
Synthetic Routes

Described in this review is a general and efficient strategy for the synthesis of macroline-related sarpagine and ajmaline alkaloids. The tetracyclic ketone in the parent system, as well as the alkoxy substituted series served as templates for the synthesis of these complex molecules. The palladium-mediated enolate cross coupling process, regiospecific hydroboration, and Tollens reaction are some of the key transformations that have been employed for further functionalization of these templates. Synthetic routes that have been improved, in order to obtain gram quantities of these alkaloids form a part of this review.

On-Line Reaction Monitoring and Mechanistic Studies by Mass Spectrometry: Negishi Cross-Coupling, Hydrogenolysis, and Reductive Amination

2014 ◽  
Vol 126 (23) ◽  
pp. 6041-6045 ◽  
Author(s):  
Xin Yan ◽  
Ewa Sokol ◽  
Xin Li ◽  
Guangtao Li ◽  
Shiqing Xu ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Reductive Amination ◽  
Cross Coupling ◽  
Reaction Monitoring ◽  
Mechanistic Studies ◽  
On Line
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