3 Ruthenium-Catalyzed Azide–Alkyne Cycloaddition (RuAAC)

2022 ◽  
Author(s):  
A. J. Paterson ◽  
T. Beke-Somfai ◽  
N. Kann
Keyword(s):  
High Selectivity ◽  
Cycloaddition Reactions ◽  
Terminal Alkynes ◽  
Organic Azides ◽  
Internal Alkynes ◽  
Ruthenium Catalysis

AbstractUnder ruthenium catalysis, 1,5-disubstituted 1,2,3-triazoles can be accessed with high selectivity from terminal alkynes and organic azides via a ruthenium-catalyzed azide–alkyne cycloaddition (RuAAC) reaction. These conditions also allow the use of internal alkynes, providing access to 1,4,5-trisubstituted 1,2,3-triazoles. This chapter reviews the scope and limitations of the RuAAC reaction, as well as selected applications. A brief mention of azide–alkyne cycloaddition reactions catalyzed by other metals is also included.

Rhodium-Catalyzed, Phosphorus(III)-Directed Hydroarylation of Internal Alkynes: Facile and Efficient Access to New Phosphine Ligands

Synlett ◽  
2020 ◽  
Author(s):  
Minyan Wang ◽  
Zhuangzhi Shi ◽  
Huanhuan Luo ◽  
Dawei Wang
Keyword(s):  
High Selectivity ◽  
Enantiomeric Excess ◽  
Phosphine Ligands ◽  
Rapid Construction ◽  
Efficient Access ◽  
Internal Alkynes ◽  
Great Progress ◽  
Chiral Phosphine Ligands ◽  
Optimized Conditions ◽  
Made In

AbstractOrganophosphines are an important class of ligands widely used in organic chemistry. Although great progress has recently been made in the rapid construction of new phosphines through Rh- or Ru-catalyzed C–H bond functionalizations, synthetic access to more diverse phosphines remains a challenge. We describe an efficient process for the rhodium-catalyzed phosphorus(III)-directed hydroarylation of internal alkynes to generate various alkenylated and 2′,6′-dialkenylated biarylphosphines with high selectivity. A range of diverse alkynes and phosphines were effectively prepared with broad functional-group compatibility under the optimized conditions. In addition, the developed protocol can be extended to modify chiral phosphine ligands, providing enantioenriched alkenylated phosphines without erosion of the enantiomeric excess.

The synthesis of five membered N-heterocycles by cycloadditions of nitroalkenes with (in)organic azides and other 1,3-dipoles

Synthesis ◽  
2021 ◽  
Author(s):  
Shandev Pookkandam Parambil ◽  
Santhini Pulikkal Veettil ◽  
Wim Dehaen
Keyword(s):  
Research Area ◽  
Cycloaddition Reactions ◽  
Powerful Method ◽  
Organic Azides

Cycloaddition reactions have emerged as rapid and powerful method for constructing heterocycles and carbocycles. [3+2] Cycloadditions of nitroalkenes with various 1,3-dipoles have been an interesting research area for many organic chemists. This review outlines the synthesis of N-substituted and NH-1,2,3-triazoles along with other five membered N-heterocycles through cycloaddition reactions of nitroalkene. 1. Introduction 2. Synthesis of 1,2,3-triazoles 2.1.Synthesis of NH-1,2,3-triazoles 2.2.Synthesis of N-substituted 1,2,3-triazoles 3. Synthesis of Pyrrolidines and Pyrroles 4. Synthesis of Pyrazoles 5. Conclusion

scholarly journals C–C (alkynylation) vs C–O (ether) bond formation under Pd/C–Cu catalysis: synthesis and pharmacological evaluation of 4-alkynylthieno[2,3-d]pyrimidines

2011 ◽  
Vol 7 ◽  
pp. 338-345 ◽  
Author(s):  
Dhilli Rao Gorja ◽  
K Shiva Kumar ◽  
K Mukkanti ◽  
Manojit Pal
Keyword(s):  
Cytotoxic Activity ◽  
Catalytic System ◽  
High Selectivity ◽  
Bond Formation ◽  
Terminal Alkynes ◽  
Ether Bond ◽  
Pharmacological Evaluation

The Pd/C–CuI–PPh3 catalytic system facilitated C–C bond formation between 4-chlorothieno[2,3-d]pyrimidines and terminal alkynes in methanol with high selectivity without generating any significant side products arising from C–O bond formation between the chloro compounds and methanol. A variety of novel 4-alkynylthieno[2,3- d]pyrimidines were prepared via alkynylation of 4-chlorothieno[2,3-d]pyrimidines in good to excellent yields. Some of the compounds synthesized were tested for cytotoxic activity in vitro.

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 Copper nanoparticles on controlled pore glass (CPG) as highly efficient heterogeneous catalysts for “click reactions”

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Abdolrahim A. Rafi ◽  
Ismail Ibrahem ◽  
Armando Córdova
Keyword(s):  
Copper Nanoparticles ◽  
Heterogeneous Catalysts ◽  
Catalyst System ◽  
Terminal Alkynes ◽  
Click Reactions ◽  
Dipolar Cycloadditions ◽  
Organic Azides ◽  
Controlled Pore Glass ◽  
Pore Glass ◽  
High Yields

AbstractWe herein report that supported copper nanoparticles (CuNPs) on commercially available controlled pore glass (CPG), which exhibit high mechanical, thermal and chemical stability as compared to other silica-based materials, serve as a useful heterogeneous catalyst system for 1,3-dipolar cycloadditions (“click” reactions) between terminal alkynes and organic azides under green chemistry conditions. The supported CuNPs-CPG catalyst exhibited a broad substrate scope and gave the corresponding triazole products in high yields. The CuNPs-CPG catalyst exhibit recyclability and could be reuced multiple times without contaminating the products with Cu.

Visible Light-Mediated [2 + 2] Cycloaddition Reactions of 1,4-Quinones and Terminal Alkynes

2019 ◽  
Vol 84 (14) ◽  
pp. 8948-8958 ◽  
Author(s):  
Shaista Sultan ◽  
Muneer-ul-Shafi Bhat ◽  
Masood Ahmad Rizvi ◽  
Bhahwal Ali Shah
Keyword(s):  
Visible Light ◽  
Cycloaddition Reactions ◽  
Terminal Alkynes
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