Platinum Complexes Bearing Bulky N-Heterocyclic Carbene Ligands as Efficient Catalysts for the Fully Selective Dimerization of Terminal Alkynes

ChemCatChem ◽  
2017 ◽  
Vol 9 (19) ◽  
pp. 3627-3631 ◽  
Author(s):  
Patrycja Żak ◽  
Małgorzata Bołt ◽  
Jan Lorkowski ◽  
Maciej Kubicki ◽  
Cezary Pietraszuk
Keyword(s):  
Platinum Complexes ◽  
Terminal Alkynes ◽  
Carbene Ligands

scholarly journals Cover Feature: Platinum Complexes Bearing Bulky N-Heterocyclic Carbene Ligands as Efficient Catalysts for the Fully Selective Dimerization of Terminal Alkynes (ChemCatChem 19/2017)

ChemCatChem ◽  
2017 ◽  
Vol 9 (19) ◽  
pp. 3619-3619
Author(s):  
Patrycja Żak ◽  
Małgorzata Bołt ◽  
Jan Lorkowski ◽  
Maciej Kubicki ◽  
Cezary Pietraszuk
Keyword(s):  
Platinum Complexes ◽  
Terminal Alkynes ◽  
Carbene Ligands

scholarly journals Cyclic(Alkyl)(Amino)Carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes

2021 ◽  
Author(s):  
Yang Gao ◽  
Sima Yazdani ◽  
Aaron Kendrick ◽  
Glen Junor ◽  
Douglas Grotjahn ◽  
...  
Keyword(s):  
High Selectivity ◽  
Building Blocks ◽  
Terminal Alkynes ◽  
Carbene Ligands ◽  
Catalytic Systems ◽  
General Solutions ◽  
Shed Light ◽  
Limited Scope

Regioselective hydrofunctionalization of alkynes represents a straightforward route to access alkenyl boronate and silane building blocks. In previously reported catalytic systems, high selectivity is achieved with a limited scope of substrates and/or reagents, with general solutions lacking. Herein, we describe a selective copper-catalyzed Markovnikov hydrofunctionalization of terminal alkynes that is facilitated by strongly donating cyclic (alkyl)(amino)carbene (CAAC) ligands. Using this method, both alkyl- and aryl-substituted alkynes are coupled with a variety of boryl and silyl reagents with high α-selectivity. The reaction is scalable, and the products are versatile intermediates that can participate in various downstream transformations. Preliminary mechanistic experiments shed light on the role of CAAC ligands in this process.

scholarly journals Cyclic(Alkyl)(Amino)Carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes

2021 ◽  
Author(s):  
Yang Gao ◽  
Sima Yazdani ◽  
Aaron Kendrick ◽  
Glen Junor ◽  
Douglas Grotjahn ◽  
...  
Keyword(s):  
High Selectivity ◽  
Building Blocks ◽  
Terminal Alkynes ◽  
Carbene Ligands ◽  
Catalytic Systems ◽  
General Solutions ◽  
Shed Light ◽  
Limited Scope

Regioselective hydrofunctionalization of alkynes represents a straightforward route to access alkenyl boronate and silane building blocks. In previously reported catalytic systems, high selectivity is achieved with a limited scope of substrates and/or reagents, with general solutions lacking. Herein, we describe a selective copper-catalyzed Markovnikov hydrofunctionalization of terminal alkynes that is facilitated by strongly donating cyclic (alkyl)(amino)carbene (CAAC) ligands. Using this method, both alkyl- and aryl-substituted alkynes are coupled with a variety of boryl and silyl reagents with high α-selectivity. The reaction is scalable, and the products are versatile intermediates that can participate in various downstream transformations. Preliminary mechanistic experiments shed light on the role of CAAC ligands in this process.

1,3,4-Trisubtituted-1,2,3-Triazol-5-ylidene 'Click' Carbene Ligands: Synthesis, Catalysis and Self-Assembly

2011 ◽  
Vol 64 (8) ◽  
pp. 1118 ◽  
Author(s):  
James D. Crowley ◽  
Ai-Lan Lee ◽  
Kelly J. Kilpin
Keyword(s):  
Metal Complexes ◽  
Self Assembly ◽  
Ring Opening ◽  
Click Reaction ◽  
Heterocyclic Carbenes ◽  
Terminal Alkynes ◽  
Carbene Ligands ◽  
Organic Azides ◽  
Self Assembled ◽  
Rapid Generation

This review examines the use of the Cu(I)-catalyzed 1,3-cycloaddition of organic azides with terminal alkynes (the CuAAC ‘click’ reaction) for development of a novel family of abnormal/mesoionic N-heterocyclic carbenes and their corresponding metal complexes. These 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes have donor properties that are intermediate between the traditional Arduengo-type imidazol-2-ylidenes and more highly σ-donating abnormal carbenes, such as imidazol-4-ylidenes or pyrazolin-4-ylidenes. Metal complexes of the 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes have been used as catalysts for a variety of reactions including the CuAAC cycloaddition, Pd cross-couplings, and ring closing/ring opening metathesis. Additionally, ‘click’ carbene ligands have been used to generate self-assembled metallo-macrocycles and novel photosensitizers. The mild, modular CuAAC approach to these ligands should allow the rapid generation of libraries of 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes that can be further exploited to generate novel catalysts, metallo-pharmaceuticals and materials.

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