An oxidative cross-coupling reaction of 4-hydroxydithiocoumarin and amines/thiols using a combination of I2 and TBHP: access to lead molecules for biomedical applications

2018 ◽  
Vol 54 (12) ◽  
pp. 1513-1516 ◽  
Author(s):  
Karuna Mahato ◽  
Neha Arora ◽  
Prasanta Ray Bagdi ◽  
Radhakrishna Gattu ◽  
Siddhartha Sankar Ghosh ◽  
...  
Keyword(s):  
Biomedical Applications ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Metal Free ◽  
Cross Coupling Reaction

Environmentally benign mild reaction conditions for the construction of new S–N/S–C/S–S bonds under metal free conditions.

The C–OH/P–H dehydrative cross-coupling for the construction of the P–C bond under metal-free conditions

2017 ◽  
Vol 19 (9) ◽  
pp. 2135-2139 ◽  
Author(s):  
Peizhong Xie ◽  
Jinyu Wang ◽  
Jing Fan ◽  
Yanan Liu ◽  
Xiangyang Wo ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Environmentally Benign ◽  
Metal Free ◽  
Cross Coupling Reaction

Herein, we report an atom-economical and environmentally benign approach for P–C bond construction via C–OH/P–H dehydrative cross-coupling reaction.

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.

ChemInform Abstract: A Transition-Metal-Free Cross-Coupling Reaction of Allylic Bromides with Aryl- and Vinylboronic Acids.

ChemInform ◽  
2012 ◽  
Vol 43 (33) ◽  
pp. no-no
Author(s):  
Mitsuhiro Ueda ◽  
Kota Nishimura ◽  
Ryo Kashima ◽  
Ilhyong Ryu
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Free ◽  
Cross Coupling Reaction

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.

ChemInform Abstract: Selective Synthesis of Partially Protected Nonsymmetric Biphenols by Reagent- and Metal-Free Anodic Cross-Coupling Reaction.

ChemInform ◽  
2016 ◽  
Vol 47 (52) ◽  
Author(s):  
Anton Wiebe ◽  
Dieter Schollmeyer ◽  
Katrin M. Dyballa ◽  
Robert Franke ◽  
Siegfried R. Waldvogel
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Selective Synthesis ◽  
Metal Free ◽  
Cross Coupling Reaction

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.

Transition metal-free tandem pyridinyl–allyl–allyl cross-coupling reaction

2017 ◽  
Vol 47 (18) ◽  
pp. 1668-1675 ◽  
Author(s):  
Lili Zhang ◽  
Zhengkai Chen ◽  
Hongli Li ◽  
Wenguang Yin ◽  
Jianfeng Xu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Free ◽  
Cross Coupling Reaction

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.

An Iodide-Mediated Transition-Metal-Free Strategy towards Unsymmetrical Diaryl Sulfides via Arylhydrazines and Thiols

Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 727-734 ◽  
Author(s):  
Farnaz Jafarpour ◽  
Mohammad Asadpour ◽  
Meysam Azizzade ◽  
Mehran Ghasemi ◽  
Saideh Rajai-Daryasarei
Keyword(s):  
Transition Metal ◽  
Room Temperature ◽  
Bond Formation ◽  
Antidepressant Drug ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Potential Utility ◽  
Metal Free ◽  
Cross Coupling Reaction ◽  
High Yields

A mild, scalable iodine-mediated oxidative cross-coupling reaction of arylhydrazines and thiols for construction of thioethers (sulfides) in the absence of any transition metals or photocatalysts is disclosed. A variety of unsymmetrical diaryl sulfides with broad substrate scope both on thiols and hydrazines were synthesized in high yields in water at room temperature. Furthermore, to demonstrate the utility of the protocol, the above C–S bond formation was applied in the synthesis of the key structure of vortioxetine as an antidepressant drug. The gram-scale outcome also added to the potential utility of this protocol.

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