Cu(II)/Proline-Catalyzed Reductive Coupling of Sulfuryl Chloride and P(O)–H for P–S–C Bond Formation

2018 ◽  
Vol 83 (3) ◽  
pp. 1532-1537 ◽  
Author(s):  
Xinghua Zhang ◽  
Dungai Wang ◽  
Duo An ◽  
Boshi Han ◽  
Xiang Song ◽  
...  
Keyword(s):  
Bond Formation ◽  
Sulfuryl Chloride ◽  
Reductive Coupling

Recent Developments in C–C Bond Formation Using Catalytic Reductive Coupling Strategies

Synthesis ◽  
2020 ◽  
Vol 52 (18) ◽  
pp. 2623-2638
Author(s):  
Joshua D. Sieber ◽  
Toolika Agrawal
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Short Review ◽  
Reductive Coupling ◽  
Recent Developments ◽  
Molecular Complexity ◽  
Metal Catalyzed ◽  
Coupling Processes ◽  
Coupling Strategies

Metal-catalyzed reductive coupling processes have emerged as a powerful methodology for the introduction of molecular complexity from simple starting materials. These methods allow for an orthogonal approach to that of redox-neutral strategies for the formation of C–C bonds by enabling cross-coupling of starting materials not applicable to redox-neutral chemistry. This short review summarizes the most recent developments in the area of metal-catalyzed reductive coupling utilizing catalyst turnover by a stoichiometric reductant that becomes incorporated in the final product.1 Introduction2 Ni Catalysis3 Cu Catalysis4 Ru, Rh, and Ir Catalysis4.1 Alkenes4.2 1,3-Dienes4.3 Allenes4.4 Alkynes4.5 Enynes5 Fe, Co, and Mn Catalysis6 Conclusion and Outlook

Carbon-carbon bond formation in the reductive coupling of nitriles at a multiply bonded dirhenium center

1988 ◽  
Vol 27 (18) ◽  
pp. 3066-3067 ◽  
Author(s):  
David Esjornson ◽  
Phillip E. Fanwick ◽  
Richard A. Walton
Keyword(s):  
Bond Formation ◽  
Reductive Coupling ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Multiply Bonded

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

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