Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers with Aryl Boronic Esters

2008 ◽  
Vol 120 (26) ◽  
pp. 4944-4947 ◽  
Author(s):  
Mamoru Tobisu ◽  
Toshiaki Shimasaki ◽  
Naoto Chatani
Keyword(s):  
Cross Coupling ◽  
Boronic Esters ◽  
Aryl Methyl

ChemInform Abstract: Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers with Aryl Boronic Esters.

ChemInform ◽  
2008 ◽  
Vol 39 (44) ◽  
Author(s):  
Mamoru Tobisu ◽  
Toshiaki Shimasaki ◽  
Naoto Chatani
Keyword(s):  
Cross Coupling ◽  
Boronic Esters ◽  
Aryl Methyl

Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers with Aryl Boronic Esters

2008 ◽  
Vol 47 (26) ◽  
pp. 4866-4869 ◽  
Author(s):  
Mamoru Tobisu ◽  
Toshiaki Shimasaki ◽  
Naoto Chatani
Keyword(s):  
Cross Coupling ◽  
Boronic Esters ◽  
Aryl Methyl

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.

The Synthesis of Pharmaceuticals: The Effective Application of Secondary Boronic Esters in Enantioselective Suzuki ‐ Miyaura Cross ‐ Coupling Reactions

2016 ◽  
Author(s):  
Jonathon Moir
Keyword(s):  
Natural Products ◽  
Human Life ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Carbon Bonds ◽  
Effective Drugs

Pharmaceuticals and drugs have become an indispensable part of human life. Presently, a myriad of different drugs are available for a variety of mental and physical health concersn. The synthesis of these drugs, however, remains an elusive and often difficult aspect of the industry. The importance of chirality, or "handedness", in the synthesis of natural products is paramount, as any given pair of enantiomers can have widely differing physiological effects. As such, the ability to control the enantioselectivity of a reaction is of the utmost importance. One example of a facile method used to form carbon-carbon bonds is the Suzuki-Miyaura cross-coupling reaction. Not only is this reaction effective at coupling primary organoboronic esters with organohalides, but recent work in the Crudden group in the Department of Chemistry has revealed an effective method of also cross-couplingchiral secondary organoboronic esters with good retention of stereochemistry. This work, the first of its kind, is crucial in developing single-handed natural products for a wide array of applications, including applications in the pharmaceutical industry. The end result is safer and more effective drugs for distribution to the general public. To expand the scope of this project, new substrates are currently being synthesized for cross-coupling applications. The overall goal is to improve upon current methodologies, while helping to meet the industrial and academic needs of the future.  

scholarly journals Transition-metal-free formal cross-coupling of aryl methyl sulfoxides and alcohols via nucleophilic activation of C-S bond

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Guolin Li ◽  
Yexenia Nieves-Quinones ◽  
Hui Zhang ◽  
Qingjin Liang ◽  
Shuaisong Su ◽  
...  
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Metal Free ◽  
Aryl Methyl

ChemInform Abstract: Copper-Catalyzed Cross-Coupling Reactions of Epoxides with gem-Diborylmethane: Access to γ-Hydroxyl Boronic Esters.

ChemInform ◽  
2016 ◽  
Vol 47 (31) ◽  
Author(s):  
Ahmed Ebrahim-Alkhalil ◽  
Zhen-Qi Zhang ◽  
Tian-Jun Gong ◽  
Wei Su ◽  
Xiao-Yu Lu ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Boronic Esters

ChemInform Abstract: Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C-O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination.

ChemInform ◽  
2016 ◽  
Vol 47 (37) ◽  
Author(s):  
Xiangqian Liu ◽  
Chien-Chi Hsiao ◽  
Indrek Kalvet ◽  
Matthias Leiendecker ◽  
Lin Guo ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Cross Coupling ◽  
Hydride Elimination ◽  
Aryl Methyl
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