Ligand-Controlled Nickel-Catalyzed Reductive Relay Cross-Coupling of Alkyl Bromides and Aryl Bromides

ACS Catalysis ◽  
2017 ◽  
Vol 8 (1) ◽  
pp. 310-313 ◽  
Author(s):  
Long Peng ◽  
Yuqiang Li ◽  
Yangyang Li ◽  
Wang Wang ◽  
Hailiang Pang ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Aryl Bromides ◽  
Alkyl Bromides

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Alkyl Bromides: Et3N as the Terminal Reductant

2016 ◽  
Vol 18 (16) ◽  
pp. 4012-4015 ◽  
Author(s):  
Zhengli Duan ◽  
Wu Li ◽  
Aiwen Lei
Keyword(s):  
Cross Coupling ◽  
Aryl Bromides ◽  
Alkyl Bromides

Photochemical Nickel-Catalyzed Reductive Migratory Cross-Coupling of Alkyl Bromides with Aryl Bromides

2018 ◽  
Vol 20 (7) ◽  
pp. 1880-1883 ◽  
Author(s):  
Long Peng ◽  
Zheqi Li ◽  
Guoyin Yin
Keyword(s):  
Cross Coupling ◽  
Aryl Bromides ◽  
Alkyl Bromides

Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions

2020 ◽  
Vol 24 (3) ◽  
pp. 231-264 ◽  
Author(s):  
Kevin H. Shaughnessy
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Wide Range ◽  
Sterically Demanding ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Phosphines are widely used ligands in transition metal-catalyzed reactions. Arylphosphines, such as triphenylphosphine, were among the first phosphines to show broad utility in catalysis. Beginning in the late 1990s, sterically demanding and electronrich trialkylphosphines began to receive attention as supporting ligands. These ligands were found to be particularly effective at promoting oxidative addition in cross-coupling of aryl halides. With electron-rich, sterically demanding ligands, such as tri-tertbutylphosphine, coupling of aryl bromides could be achieved at room temperature. More importantly, the less reactive, but more broadly available, aryl chlorides became accessible substrates. Tri-tert-butylphosphine has become a privileged ligand that has found application in a wide range of late transition-metal catalyzed coupling reactions. This success has led to the use of numerous monodentate trialkylphosphines in cross-coupling reactions. This review will discuss the general properties and features of monodentate trialkylphosphines and their application in cross-coupling reactions of C–X and C–H bonds.

Solvent-free palladium-catalyzed C–O cross-coupling of aryl bromides with phenols

2021 ◽  
Vol 31 (3) ◽  
pp. 409-411
Author(s):  
Sergey A. Rzhevskiy ◽  
Maxim A. Topchiy ◽  
Vasilii N. Bogachev ◽  
Lidiya I. Minaeva ◽  
Ilia R. Cherkashchenko ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Solvent Free ◽  
Aryl Bromides ◽  
Palladium Catalyzed

scholarly journals Reductive Cross-Coupling of Conjugated Arylalkenes and Aryl Bromides with Hydrosilanes by Cooperative Palladium/Copper Catalysis

2016 ◽  
Vol 55 (21) ◽  
pp. 6275-6279 ◽  
Author(s):  
Kazuhiko Semba ◽  
Kenta Ariyama ◽  
Hong Zheng ◽  
Ryohei Kameyama ◽  
Shigeyoshi Sakaki ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Copper Catalysis ◽  
Aryl Bromides

scholarly journals Microwave-Enhanced Cross-Coupling Reactions Involving Alkynyltrifluoroborates with Aryl Bromides

Molecules ◽  
2013 ◽  
Vol 18 (2) ◽  
pp. 1755-1761 ◽  
Author(s):  
Vitali Coltuclu ◽  
Eric Dadush ◽  
Abhijit Naravane ◽  
George Kabalka
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides

Scope of the Desulfinylative Palladium-Catalyzed Cross-Coupling of Aryl Sulfinates with Aryl Bromides

Synthesis ◽  
2013 ◽  
Vol 45 (05) ◽  
pp. 694-702 ◽  
Author(s):  
Pat Forgione ◽  
Dirk Ortgies ◽  
Alexandre Barthelme ◽  
Sara Aly ◽  
Brigitte Desharnais ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Aryl Bromides ◽  
Palladium Catalyzed

scholarly journals Protecting group-free, selective cross-coupling of alkyltrifluoroborates with borylated aryl bromides via photoredox/nickel dual catalysis

2015 ◽  
Vol 112 (39) ◽  
pp. 12026-12029 ◽  
Author(s):  
Yohei Yamashita ◽  
John C. Tellis ◽  
Gary A. Molander
Keyword(s):  
Small Molecules ◽  
Functional Group ◽  
Cross Coupling ◽  
Differential Protection ◽  
Coupling Reactions ◽  
Protecting Group ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Rapid Construction ◽  
Metal Catalyzed

Orthogonal reactivity modes offer substantial opportunities for rapid construction of complex small molecules. However, most strategies for imparting orthogonality to cross-coupling reactions rely on differential protection of reactive sites, greatly reducing both atom and step economies. Reported here is a strategy for orthogonal cross-coupling wherein a mechanistically distinct activation mode for transmetalation of sp3-hybridized organoboron reagents enables C-C bond formation in the presence of various protected and unprotected sp2-hybridized organoborons. This manifold has the potential for broad application, because orthogonality is inherent to the activation mode itself. The diversification potential of this platform is shown in the rapid elaboration of a trifunctional lynchpin through various transition metal-catalyzed processes without nonproductive deprotection or functional group manipulation steps.

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