scholarly journals Multi-Label Classification Models for the Prediction of Cross-Coupling Reaction Conditions

2020 ◽  
Author(s):  
Michael Maser ◽  
Alexander Cui ◽  
Serim Ryou ◽  
Travis DeLano ◽  
Yisong Yue ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Learning Task ◽  
Gradient Boosting ◽  
Context Aware ◽  
Reaction Conditions ◽  
Convolutional Networks ◽  
Ranking Models ◽  
Cross Coupling Reaction ◽  
Reaction Level

<div><div><div><p>Machine-learned ranking models have been developed for the prediction of substrate-specific cross-coupling reaction conditions. Datasets of published reactions were curated for Suzuki, Negishi, and C–N couplings, as well as Pauson–Khand reactions. String, descriptor, and graph encodings were tested as input representations, and models were trained to predict the set of conditions used in a reaction as a binary vector. Unique reagent dictionaries categorized by expert-crafted reaction roles were constructed for each dataset, leading to context-aware predictions. We find that relational graph convolutional networks and gradient-boosting machines are very effective for this learning task, and we disclose a novel reaction-level graph-attention operation in the top-performing model.</p></div></div></div>

scholarly journals Multi-Label Classification Models for the Prediction of Cross-Coupling Reaction Conditions

2020 ◽  
Author(s):  
Michael Maser ◽  
Alexander Cui ◽  
Serim Ryou ◽  
Travis DeLano ◽  
Yisong Yue ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Learning Task ◽  
Gradient Boosting ◽  
Context Aware ◽  
Reaction Conditions ◽  
Convolutional Networks ◽  
Ranking Models ◽  
Cross Coupling Reaction ◽  
Reaction Level

<div><div><div><p>Machine-learned ranking models have been developed for the prediction of substrate-specific cross-coupling reaction conditions. Datasets of published reactions were curated for Suzuki, Negishi, and C–N couplings, as well as Pauson–Khand reactions. String, descriptor, and graph encodings were tested as input representations, and models were trained to predict the set of conditions used in a reaction as a binary vector. Unique reagent dictionaries categorized by expert-crafted reaction roles were constructed for each dataset, leading to context-aware predictions. We find that relational graph convolutional networks and gradient-boosting machines are very effective for this learning task, and we disclose a novel reaction-level graph-attention operation in the top-performing model.</p></div></div></div>

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: Tetraorganosilanes for the practical cross-coupling reaction

2006 ◽  
Vol 78 (2) ◽  
pp. 435-440 ◽  
Author(s):  
Yoshiaki Nakao ◽  
Akhila K. Sahoo ◽  
Hidekazu Imanaka ◽  
Akira Yada ◽  
Tamejiro Hiyama
Keyword(s):  
Functional Groups ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Hydroxyl Group ◽  
Axial Position ◽  
Silyl Ether ◽  
Intramolecular Coordination ◽  
Reaction Conditions ◽  
Diverse Range ◽  
Cross Coupling Reaction

Readily accessible and highly stable alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes cross-couple with various aryl and alkenyl halides under mild reaction conditions employing K2CO3 as a base at 35-80 °C. The reaction tolerates a diverse range of functional groups including silyl protections. The silicon residue, cyclic silyl ether, is readily recovered and reused on a gram-scale synthesis. Intramolecular coordination of a proximal hydroxyl group is considered to efficiently form pentacoordinated silicates having a transferable group at an axial position.

Optimizing chemical reaction conditions using deep learning: a case study for the Suzuki–Miyaura cross-coupling reaction

2020 ◽  
Vol 7 (16) ◽  
pp. 2269-2277
Author(s):  
Zunyun Fu ◽  
Xutong Li ◽  
Zhaohui Wang ◽  
Zhaojun Li ◽  
Xiaohong Liu ◽  
...  
Keyword(s):  
Mechanical Properties ◽  
Deep Learning ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Quantum Mechanical ◽  
Reaction Conditions ◽  
Cross Coupling Reaction ◽  
Deep Learning Model ◽  
Optimal Reaction

Deep learning was used to optimize chemical reactions with the quantum mechanical properties of chemical contexts and reaction conditions as inputs. The trained deep learning model determines optimal reaction conditions by in silico exploration of accessible reaction space.

scholarly journals A convenient route to symmetrically and unsymmetrically substituted 3,5-diaryl-2,4,6-trimethylpyridines via Suzuki–Miyaura cross-coupling reaction

2016 ◽  
Vol 12 ◽  
pp. 835-845 ◽  
Author(s):  
Dariusz Błachut ◽  
Joanna Szawkało ◽  
Zbigniew Czarnocki
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
High Yield ◽  
Reaction Conditions ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction ◽  
Convenient Route

A series of differently substituted 3,5-diaryl-2,4,6-trimethylpyridines were prepared and characterized using the Suzuki–Miyaura coupling reaction with accordingly selected bromo-derivatives and arylboronic acids. The reaction conditions were carefully optimized allowing high yield of isolated products and also the construction of unsymmetrically substituted diarylpyridines, difficult to access by other methods.

Dimerization of Aromatic Compounds Using Palladium-Carbon-Catalyzed Suzuki–Miyaura Cross-Coupling by One-Pot Synthesis

Synlett ◽  
2018 ◽  
Vol 29 (06) ◽  
pp. 779-784 ◽  
Author(s):  
Guoliang Chen ◽  
Fangyu Du ◽  
Qifan Zhou ◽  
Dongdong Liu ◽  
Ting Fang ◽  
...  
Keyword(s):  
Aromatic Compounds ◽  
Functional Group ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Potassium Acetate ◽  
Carbon Catalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reaction ◽  
High Yields

The aromatic dimers play a significant role in many aspects. Herein, we report a simple palladium-carbon catalyst that is highly effective for the dimerization of brominated aromatic compounds under mild conditions using abundant brominated aromatic compounds, bis(pinacolate)diboron and potassium acetate by a ‘one-pot’ method. This process, which we believe proceeds via a Suzuki–Miyaura cross-coupling reaction mechanism, allows access to a variety of aromatic compounds under mild reaction conditions and has a good functional group tolerance with moderate to high yields.

scholarly journals Cyclopentadithiophene polymers synthesised via Suzuki-Miyaura polymerisation of MIDA boronate esters

2020 ◽  
Vol 1 ◽  
Author(s):  
Josue Ayuso-Carrillo
Keyword(s):  
Conjugated Polymers ◽  
Organic Electronics ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Reaction Conditions ◽  
Boronate Esters ◽  
Boronate Ester ◽  
Cross Coupling Reaction ◽  
Synthetic Routes ◽  
Methyliminodiacetic Acid

AbstractCyclopentadithiophene (CPDT), a Csp3-bridged bithiophene heteroaromatic unit, displays interesting properties when it is embedded in the repeating units of π-conjugated polymers, and they are applied in organic electronics devices. Common synthetic routes to CPDT-derived polymers rely on toxic methodologies whilst alternative non-toxic strategies such as the Suzuki-Miyaura reaction have been less studied. In this report we demonstrate that the use of a N-methyliminodiacetic acid (MIDA) boronate ester-derived CPDT monomer allows the efficient formation of poly(cyclopentadithiophene) homopolymer under Suzuki-Miyaura cross-coupling reaction conditions. Thus, the use of MIDA boronate esters might be extended to other organic units to design and construct a plethora of π-conjugated polymers.

Synthesis of Phenylferrocene in Supercritical Carbon Dioxide

2012 ◽  
Vol 550-553 ◽  
pp. 639-642
Author(s):  
Fawang Li ◽  
Quan Ling Suo ◽  
Hai Long Hong ◽  
Li Min Han
Keyword(s):  
Carbon Dioxide ◽  
Polyethylene Glycol ◽  
Organic Solvent ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Cross Coupling Reaction ◽  
Ligand Free ◽  
Phenylboronic Acids

The environmentally benign Suzuki cross-coupling reaction was developed by using ScCO2(Supercritical CO2) instead of traditionally organic solvent. In the paper the compound phenylferrocene was synthesized by the Suzuki cross-coupling reaction of iodoferrocene and phenylboronic acids in ScCO2/PEG (polyethylene glycol) with excellent yield ratio in the presence of ligand-free Pd/C catalyst and K2CO3.1.5H2O as base. The Pd/C catalyst can be reused by simply washing sequence and CO2can be recycled after depressurization. The catalytic reaction conditions were optimized in the reaction using ScCO2as solvent.

Dual photoredox and nickel-catalyzed desymmetric C–O coupling reactions: visible light-mediated enantioselective synthesis of 1,4-benzodioxanes

2018 ◽  
Vol 5 (21) ◽  
pp. 3098-3102 ◽  
Author(s):  
Quan-Quan Zhou ◽  
Fu-Dong Lu ◽  
Dan Liu ◽  
Liang-Qiu Lu ◽  
Wen-Jing Xiao
Keyword(s):  
Visible Light ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Coupling Reactions ◽  
Nickel Catalysis ◽  
Reaction Conditions ◽  
Cross Coupling Reaction

Chiral 2,2′-bipyridine ligands are key to success in an enantioselective desymmetric C–O cross coupling reaction via dual visible light photoredox and nickel catalysis, resulting in chiral 1,4-benzodioxanes under mild reaction conditions.

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