A Unique Catalyst Effects the Rapid Room-Temperature Cross-Coupling of Organozinc Reagents with Carboxylic Acid Fluorides, Chlorides, Anhydrides, and Thioesters

2004 ◽  
Vol 126 (49) ◽  
pp. 15964-15965 ◽  
Author(s):  
Yongda Zhang ◽  
Tomislav Rovis
Keyword(s):  
Carboxylic Acid ◽  
Room Temperature ◽  
Cross Coupling ◽  
Organozinc Reagents ◽  
Acid Fluorides

Cross-Coupling of N-Allylic Sulfonimides with Organozinc Reagents at Room Temperature

2012 ◽  
Vol 2012 (22) ◽  
pp. 4107-4109 ◽  
Author(s):  
Xiang-Ling Tang ◽  
Zhao Wu ◽  
Man-Bo Li ◽  
Yonghong Gu ◽  
Shi-Kai Tian
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Organozinc Reagents

ChemInform Abstract: Cross-Coupling of N-Allylic Sulfonimides with Organozinc Reagents at Room Temperature.

ChemInform ◽  
2013 ◽  
Vol 44 (2) ◽  
pp. no-no
Author(s):  
Xiang-Ling Tang ◽  
Zhao Wu ◽  
Man-Bo Li ◽  
Yonghong Gu ◽  
Shi-Kai Tian
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Organozinc Reagents

Room-Temperature Negishi Cross-Coupling of Unactivated Alkyl Bromides with Alkyl Organozinc Reagents Utilizing a Pd/N-Heterocyclic Carbene Catalyst

2005 ◽  
Vol 70 (21) ◽  
pp. 8503-8507 ◽  
Author(s):  
Niloufar Hadei ◽  
Eric Assen B. Kantchev ◽  
Christopher J. O'Brien ◽  
Michael G. Organ
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Alkyl Bromides ◽  
Organozinc Reagents

Recent Advances in Cross-Couplings of Functionalized Organozinc Reagents

Synthesis ◽  
2021 ◽  
Author(s):  
Baosheng Wei ◽  
Paul Knochel
Keyword(s):  
Transition Metal ◽  
Room Temperature ◽  
Cross Coupling ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Iron Catalysts ◽  
Organic Azides ◽  
Recent Advances ◽  
Organozinc Reagents

Cross-couplings involving organozinc reagents require usually a Pd-catalysis (Negishi cross-coupling), however, uncatalyzed cross-couplings of zinc organometallics proceed well in the absence of transition-metal catalysts with reactive electrophiles such as benzal 1,1-diacetates, benzhydryl acetates, and iminium trifluoroacetates. Also, organozinc compounds undergo C-N bond formations with O-benzoylhydroxylamines or organic azides in the presence of cobalt- or iron-catalysts. Besides, highly diastereoselective and enantioselective cross-couplings can be readily performed with room-temperature configurationally stable alkylzinc species producing diastereoselectively and enantiomerically enriched products. Finally, highly regioselective magnesiations of functionalized arenes and heteroarenes undergo Negishi (after transmetalation with ZnCl2) or Cu-catalyzed cross-couplings. 1 Introduction 2 Uncatalyzed Cross-Couplings of Organozinc Reagents with Highly Electrophilic Partners 3 Iron- and Cobalt-catalyzed Aminations Using Organozinc Reagents 4 Stereo- and Regioselective Cross-couplings of Organozinc Reagents 5 Conclusion

scholarly journals Room-Temperature Negishi Cross-Coupling of Unactivated Alkyl Bromides with Alkyl Organozinc Reagents Utilizing a Pd/N-Heterocyclic Carbene Catalyst.

ChemInform ◽  
2006 ◽  
Vol 37 (9) ◽  
Author(s):  
Niloufar Hadei ◽  
Eric Assen B. Kantchev ◽  
Christopher J. O'Brien ◽  
Michael G. Organ
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Alkyl Bromides ◽  
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>

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