Aqueous Suzuki Coupling Reactions of Basic Nitrogen-Containing Substrates in the Absence of Added Base and Ligand: Observation of High Yields under Acidic Conditions

2016 ◽  
Vol 81 (18) ◽  
pp. 8520-8529 ◽  
Author(s):  
Zhao Li ◽  
Carol Gelbaum ◽  
Jason S. Fisk ◽  
Bruce Holden ◽  
Arvind Jaganathan ◽  
...  
Keyword(s):  
Suzuki Coupling ◽  
Coupling Reactions ◽  
Basic Nitrogen ◽  
Acidic Conditions ◽  
High Yields

Pd-Catalyzed Suzuki coupling reactions of aryl halides containing basic nitrogen centers with arylboronic acids in water in the absence of added base

2017 ◽  
Vol 41 (24) ◽  
pp. 15420-15432 ◽  
Author(s):  
Zhao Li ◽  
Carol Gelbaum ◽  
Zachary S. Campbell ◽  
Paul C. Gould ◽  
Jason S. Fisk ◽  
...  
Keyword(s):  
Suzuki Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Arylboronic Acids ◽  
Suzuki Reactions ◽  
Basic Nitrogen ◽  
Acidic Conditions

Successful Suzuki reactions of basic nitrogen containing aryl chlorides/bromides with arylboronic acids in water without added base, partially or entirely under acidic conditions.

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

Efficient Copper-Catalysed Synthesis of Carbazoles by Double N-Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air

Synlett ◽  
2021 ◽  
Author(s):  
Tran Quang Hung ◽  
Tuan Thanh Dang ◽  
Peter Langer ◽  
Ha Nam Do ◽  
Nguyen Minh Quan ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Aliphatic Amines ◽  
Primary Amines ◽  
Coupling Reactions ◽  
Carbazole Derivatives ◽  
High Yields

AbstractAn efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C–N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.

scholarly journals Synthesis and Antiproliferative Activity of Phosphorus Substituted 4-Cyanooxazolines, 2-Aminocyanooxazolines, 2-Iminocyanooxazolidines and 2-Aminocyanothiazolines by Rearrangement of Cyanoaziridines

Molecules ◽  
2021 ◽  
Vol 26 (14) ◽  
pp. 4265
Author(s):  
Victor Carramiñana ◽  
Ana M. Ochoa de Ochoa de Retana ◽  
Francisco Palacios ◽  
Jesús M. de los de los Santos
Keyword(s):  
Ring Opening ◽  
Human Lung ◽  
Ring Expansion ◽  
Moderate Activity ◽  
A549 Cell Line ◽  
One Pot ◽  
Acidic Conditions ◽  
Lung Adenocarcinoma A549 ◽  
High Yields

Several phosphorus-substituted N-acylated cyanoaziridines 2 and N-carbamoylated cyanoziridines 5 were prepared in good to high yields. N-Acylated cyanoaziridines 2 were used, after ring expansion, in an efficient synthesis of oxazoline derivative 3a and in a completely regio-controlled reaction in the presence of NaI. Conversely, N-carbamoyl cyanoaziridines 5 reacted with NaI to obtain a regioisomeric mixture of 2-aminocyanooxazolines 7. Mild acidic conditions can be used for the isomerization of N-thiocarbamoyl cyanoaziridine 6a into a 2-aminocyanothiazoline derivative 8a by using BF3·OEt2 as a Lewis acid. Likewise, a one pot reaction of NH-cyanoaziridines 1 with isocyanates obtained 2-iminocyanooxazolidines 9 regioselectively. This synthetic methodology involves the addition of isocyanates to starting cyanoaziridines to obtain N-carbamoyl cyanoaziridines 5, which after the ring opening, reacts with a second equivalent of isocyanate to give the final 2-imino cyanooxazolidines 9. In addition, the cytotoxic effect on the cell lines derived from human lung adenocarcinoma (A549) was also screened. 2-Iminooxazolidines 9 exhibited moderate activity against the A549 cell line in vitro. Furthermore, a selectivity towards cancer cells (A549) over non-malignant cells (MCR-5) was detected.

ChemInform Abstract: Synthesis of Triphenylamine-Modified Arylates and Ketones via Suzuki Coupling Reactions.

ChemInform ◽  
2011 ◽  
Vol 42 (32) ◽  
pp. no-no
Author(s):  
Jian Wang ◽  
Chang-Jian Yang ◽  
Hua-Nan Peng ◽  
Yang-Sheng Deng ◽  
Xi-Cun Gao
Keyword(s):  
Suzuki Coupling ◽  
Coupling Reactions

Organostannoxane-Supported Palladium Nanoparticles. Highly Efficient Catalysts for Suzuki-Coupling Reactions

2009 ◽  
Vol 28 (20) ◽  
pp. 5883-5888 ◽  
Author(s):  
Vadapalli Chandrasekhar ◽  
Ramakirushnan Suriya Narayanan ◽  
Pakkirisamy Thilagar
Keyword(s):  
Palladium Nanoparticles ◽  
Suzuki Coupling ◽  
Coupling Reactions ◽  
Highly Efficient ◽  
Supported Palladium
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