ChemInform Abstract: Metal-Catalyzed Cross-Coupling of Terminal Alkynes with Different Carbene Precursors

ChemInform ◽  
2016 ◽  
Vol 47 (18) ◽  
Author(s):  
Jiuwei Che ◽  
Dong Xing ◽  
Wenhao Hu
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes ◽  
Metal Catalyzed

scholarly journals Progress in Transition-Metal-Catalyzed Oxidative Cross-Coupling of Terminal Alkynes

2014 ◽  
Vol 34 (1) ◽  
pp. 81
Author(s):  
Congxia Zhang ◽  
Nana Li ◽  
Xing Li ◽  
Honghong Chang ◽  
Qiang Liu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

scholarly journals Copper-catalyzed enantioselective Sonogashira-type oxidative cross-coupling of unactivated C(sp3)−H bonds with alkynes

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Zhen-Hua Zhang ◽  
Xiao-Yang Dong ◽  
Xuan-Yi Du ◽  
Qiang-Shuai Gu ◽  
Zhong-Liang Li ◽  
...  
Keyword(s):  
Transition Metal ◽  
Alkyl Radical ◽  
Cross Coupling ◽  
Cinchona Alkaloid ◽  
Terminal Alkynes ◽  
Radical Species ◽  
Bond Functionalization ◽  
Versatile Tool ◽  
Metal Catalyzed

AbstractTransition metal-catalyzed enantioselective Sonogashira-type oxidative C(sp3)—C(sp) coupling of unactivated C(sp3)−H bonds with terminal alkynes has remained a prominent challenge. The difficulties mainly stem from the regiocontrol in unactivated C(sp3)—H bond functionalization and the inhibition of readily occurring Glaser homocoupling of terminal alkynes. Here, we report a copper/chiral cinchona alkaloid-based N,N,P-ligand catalyst for asymmetric oxidative cross-coupling of unactivated C(sp3)—H bonds with terminal alkynes in a highly regio-, chemo-, and enantioselective manner. The use of N-fluoroamide as a mild oxidant is essential to site-selectively generate alkyl radical species while efficiently avoiding Glaser homocoupling. This reaction accommodates a range of (hetero)aryl and alkyl alkynes; (hetero)benzylic and propargylic C(sp3)−H bonds are all applicable. This process allows expedient access to chiral alkynyl amides/aldehydes. More importantly, it also provides a versatile tool for the construction of chiral C(sp3)—C(sp), C(sp3)—C(sp2), and C(sp3)—C(sp3) bonds when allied with follow-up transformations.

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.

scholarly journals Atom-Economical Cross-Coupling of Internal and Terminal Alkynes to Access 1,3-Enynes

2021 ◽  
Author(s):  
Mingyu Liu ◽  
Tianhua Tang ◽  
Omar Apolinar ◽  
Rei Matsuura ◽  
Carl A. Busacca ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes
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