Nickel-Catalyzed Cross-Coupling of Aryl 2-Pyridyl Ethers with Organozinc Reagents: Removal of the Directing Group via Cleavage of the Carbon–Oxygen Bonds

2021 ◽  
Vol 86 (3) ◽  
pp. 2235-2243
Author(s):  
Wei-Can Dai ◽  
Bo Yang ◽  
Shi-He Xu ◽  
Zhong-Xia Wang
Keyword(s):  
Cross Coupling ◽  
Directing Group ◽  
Organozinc Reagents

Modular, Stereocontrolled Cβ–H/Cα–C Activation of Alkyl Carboxylic Acids

2019 ◽  
Author(s):  
Ming Shang ◽  
Karla S. Feu ◽  
Julien C. Vantourout ◽  
Lisa M. Barton ◽  
Heather L. Osswald ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Heterocyclic Compounds ◽  
Cross Coupling ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Carbon Centers ◽  
Drug Candidates ◽  
Rapid Diversification ◽  
Directing Group ◽  
Compound Series

<div> <div> <div> <p>The union of two powerful transformations, directed C–H activation and decarboxylative cross-coupling, for the enantioselective synthesis of vicinally functionalized alkyl, carbocyclic, and heterocyclic compounds is described. Starting from simple carboxylic acid building blocks, this modular sequence exploits the residual directing group to access more than 50 scaffolds that would be otherwise extremely difficult to prepare. The tactical use of these two transformations accomplishes a formal vicinal difunctionalization of carbon centers in a way that is modular and thus amenable to rapid diversity incorporation. A simplification of routes to known preclinical drug candidates is presented along with the rapid diversification of an antimalarial compound series. </p> </div> </div> </div>

scholarly journals Enantioselective Radical Addition/Cross‐Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents

2019 ◽  
Vol 58 (40) ◽  
pp. 14245-14249 ◽  
Author(s):  
Matteo Chierchia ◽  
Peilin Xu ◽  
Gabriel J. Lovinger ◽  
James P. Morken
Keyword(s):  
Cross Coupling ◽  
Radical Addition ◽  
Alkyl Iodides ◽  
Organozinc Reagents

scholarly journals Cross‐Coupling of Aryl/Alkenyl Pivalates with Organozinc Reagents through Nickel‐Catalyzed CO Bond Activation under Mild Reaction Conditions

2009 ◽  
Vol 48 (8) ◽  
pp. 1351-1351
Author(s):  
Bi‐Jie Li ◽  
Yi‐Zhou Li ◽  
Xing‐Yu Lu ◽  
Jia Liu ◽  
Bing‐Tao Guan ◽  
...  
Keyword(s):  
Bond Activation ◽  
Cross Coupling ◽  
Reaction Conditions ◽  
Organozinc Reagents

A Mild Negishi Cross-Coupling of 2-Heterocyclic Organozinc Reagents and Aryl Chlorides

2010 ◽  
Vol 75 (23) ◽  
pp. 8330-8332 ◽  
Author(s):  
Michael R. Luzung ◽  
Jigar S. Patel ◽  
Jingjun Yin
Keyword(s):  
Cross Coupling ◽  
Aryl Chlorides ◽  
Organozinc Reagents

Pd-PEPPSI-IPentCl: A Highly Effective Catalyst for the Selective Cross-Coupling of Secondary Organozinc Reagents

2012 ◽  
Vol 51 (45) ◽  
pp. 11354-11357 ◽  
Author(s):  
Matthew Pompeo ◽  
Robert D. J. Froese ◽  
Niloufar Hadei ◽  
Michael G. Organ
Keyword(s):  
Cross Coupling ◽  
Effective Catalyst ◽  
Highly Effective ◽  
Organozinc Reagents

Nickel-Catalyzed Cross-Coupling of Aryl Fluorides and Organozinc Reagents

2014 ◽  
Vol 79 (10) ◽  
pp. 4285-4292 ◽  
Author(s):  
Feng Zhu ◽  
Zhong-Xia Wang
Keyword(s):  
Cross Coupling ◽  
Organozinc Reagents
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