Ligand- and Base-Free Copper(II)-Catalyzed C−N Bond Formation:  Cross-Coupling Reactions of Organoboron Compounds with Aliphatic Amines and Anilines

2003 ◽  
Vol 5 (23) ◽  
pp. 4397-4400 ◽  
Author(s):  
Tan D. Quach ◽  
Robert A. Batey
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Aliphatic Amines ◽  
Coupling Reactions ◽  
Organoboron Compounds ◽  
Cross Coupling Reactions

Cu-Catalyzed cross-coupling reactions of epoxides with organoboron compounds

2015 ◽  
Vol 51 (12) ◽  
pp. 2388-2391 ◽  
Author(s):  
Xiao-Yu Lu ◽  
Chu-Ting Yang ◽  
Jing-Hui Liu ◽  
Zheng-Qi Zhang ◽  
Xi Lu ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Organoboron Compounds ◽  
Cross Coupling Reactions

Cu-catalyzed cross-coupling reactions of epoxides and aziridines with organoboron compounds.

Copper-catalyzed cross-coupling reactions for C–P bond formation

RSC Advances ◽  
2015 ◽  
Vol 5 (65) ◽  
pp. 52824-52831 ◽  
Author(s):  
Hui Zhang ◽  
Xue-Yan Zhang ◽  
Dao-Qing Dong ◽  
Zu-Li Wang
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Phosphorus Compounds ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Phosphorus compounds are important compounds in many areas.

scholarly journals Computational Insights into Intramolecular Cross-Coupling of Quaternary Borate Salts

2021 ◽  
Author(s):  
Florian Matz ◽  
Arif Music ◽  
Dorian Didier ◽  
Thomas C. Jagau
Keyword(s):  
Organic Synthesis ◽  
Energy Barrier ◽  
Density Functional ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupled Cluster ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Product Distributions ◽  
Borate Salts

Cross-coupling reactions for C-C bond formation represent a cornerstone of organic synthesis. In most cases, they make use of transition metals, which has several downsides. Recently, metal-free alternatives relying on electrochemistry have gained interest. One example of such a reaction is the oxidation of tetraorganoborate salts that initiates aryl-aryl and aryl-alkenyl couplings with promising selectivities. This work investigates the mechanism of this reaction computationally using density functional and coupled-cluster theory. Our calculations reveal a distinct difference between aryl-alkenyl and aryl-aryl couplings: While C-C bond formation occurs irreversibly and without an energy barrier if an alkenyl residue is involved, many intermediates can be identified in aryl-aryl couplings. In the latter case, intramolecular transitions between reaction paths leading to different products are possible. Based on the energy differences between these intermediates, we develop a kinetic model to estimate product distributions for aryl-aryl couplings.<br>

scholarly journals Computational Insights into Intramolecular Cross-Coupling of Quaternary Borate Salts

2021 ◽  
Author(s):  
Florian Matz ◽  
Arif Music ◽  
Dorian Didier ◽  
Thomas C. Jagau
Keyword(s):  
Organic Synthesis ◽  
Energy Barrier ◽  
Density Functional ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupled Cluster ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Product Distributions ◽  
Borate Salts

Cross-coupling reactions for C-C bond formation represent a cornerstone of organic synthesis. In most cases, they make use of transition metals, which has several downsides. Recently, metal-free alternatives relying on electrochemistry have gained interest. One example of such a reaction is the oxidation of tetraorganoborate salts that initiates aryl-aryl and aryl-alkenyl couplings with promising selectivities. This work investigates the mechanism of this reaction computationally using density functional and coupled-cluster theory. Our calculations reveal a distinct difference between aryl-alkenyl and aryl-aryl couplings: While C-C bond formation occurs irreversibly and without an energy barrier if an alkenyl residue is involved, many intermediates can be identified in aryl-aryl couplings. In the latter case, intramolecular transitions between reaction paths leading to different products are possible. Based on the energy differences between these intermediates, we develop a kinetic model to estimate product distributions for aryl-aryl couplings.<br>

scholarly journals Biocatalytic oxidative cross-coupling reactions for biaryl bond formation

2021 ◽  
Author(s):  
Lara Zetzsche ◽  
Jessica Yazarians ◽  
Suman Chakrabarty ◽  
Meagan Hinze ◽  
April Lukowski ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Bond Formation ◽  
Cross Coupling ◽  
Building Blocks ◽  
Coupling Reactions ◽  
Cytochrome P450 Enzymes ◽  
Cross Coupling Reactions ◽  
Site Selectivity ◽  
Valuable Compounds ◽  
Selective Process

Despite their varied purposes, many indispensable molecules in medicine, materials, and asymmetric catalysis share a biaryl core. The necessity of joining arene building blocks to access these valuable compounds has inspired multiple approaches for biaryl bond formation and challenged chemists to develop increasingly concise and robust methods for this task. Oxidative coupling of two C–H bonds offers an efficient strategy for the formation of a biaryl C–C bond, however, fundamental challenges remain in controlling the reactivity and selectivity for uniting a given pair of substrates. Biocatalytic oxidative cross-coupling reactions have the potential to overcome limitations inherent to small molecule- mediated methods by providing a paradigm with catalyst-controlled selectivity. In this article, we disclose a strategy for biocatalytic cross-coupling through oxidative C–C bond formation using cytochrome P450 enzymes. We demonstrate the ability to catalyze cross-coupling reactions on a panel of phenolic substrates using natural P450 catalysts. Moreover, we engineer a P450 to possess the desired reactivity, site- selectivity, and atroposelectivity by transforming a low-yielding, unselective reaction into a highly efficient and selective process. This streamlined method for constructing sterically hindered biaryl bonds provides a programmable platform for assembling molecules with catalyst-controlled reactivity and selectivity.

Deoxygenative Transition-Metal-Promoted Reductive Coupling and Cross-Coupling of Alcohols and Epoxides

Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 267-278
Author(s):  
Kenneth M. Nicholas ◽  
Chandrasekhar Bandari
Keyword(s):  
Transition Metal ◽  
Bond Activation ◽  
Bond Formation ◽  
Cross Coupling ◽  
Transition Metal Catalysts ◽  
Coupling Reactions ◽  
Reductive Coupling ◽  
Practical Applications ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond

AbstractThe prospective utilization of abundant, CO2-neutral, renewable feedstocks is driving the discovery and development of new reactions that refunctionalize oxygen-rich substrates such as alcohols and polyols through C–O bond activation. In this review, we highlight the development of transition-metal-promoted reactions of renewable alcohols and epoxides that result in carbon–carbon bond-formation. These include reductive self-coupling reactions and cross-coupling reactions of alcohols with alkenes and arene derivatives. Early approaches to reductive couplings employed stoichiometric amounts of low-valent transition-metal reagents to form the corresponding hydrocarbon dimers. More recently, the use of redox-active transition-metal catalysts together with a reductant has enhanced the practical applications and scope of the reductive coupling of alcohols. Inclusion of other reaction partners with alcohols such as unsaturated hydrocarbons and main-group organometallics has further expanded the diversity of carbon skeletons accessible and the potential for applications in chemical synthesis. Catalytic reductive coupling and cross-coupling reactions of epoxides are also highlighted. Mechanistic insights into the means of C–O activation and C–C bond formation, where available, are also highlighted.1 Introduction2 Stoichiometric Reductive Coupling of Alcohols3 Catalytic Reductive Coupling of Alcohols3.1 Heterogeneous Catalysis3.2 Homogeneous Catalysis4 Reductive Cross-Coupling of Alcohols4.1 Reductive Alkylation4.2 Reductive Addition to Olefins5 Epoxide Reductive Coupling Reactions6 Conclusions and Future Directions

Sign in / Sign up

Export Citation Format

Share Document