Mechanism and reactivity of catalytic propargylic substitution reactions via metal–allenylidene intermediates: a theoretical perspective

2018 ◽  
Vol 8 (1) ◽  
pp. 12-25 ◽  
Author(s):  
Ken Sakata ◽  
Yoshiaki Nishibayashi
Keyword(s):  
Transition Metal ◽  
Theoretical Perspective ◽  
Point Of View ◽  
Theoretical Point ◽  
Substitution Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Propargylic Substitution

The mechanism and reactivity of transition metal-catalyzed propargylic substitution reactions are summarized from a theoretical point of view.

Transition-Metal-Catalyzed Synthesis of Organophosphorus Compounds Involving P–P Bond Cleavage

Synthesis ◽  
2020 ◽  
Vol 52 (19) ◽  
pp. 2795-2806 ◽  
Author(s):  
Mieko Arisawa
Keyword(s):  
Transition Metal ◽  
Organophosphorus Compounds ◽  
Bond Cleavage ◽  
Palladium Complexes ◽  
Addition Reactions ◽  
Phosphonium Salts ◽  
Substitution Reactions ◽  
Sulfonic Acids ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Organophosphorus compounds are used as drugs, pesticides, detergents, food additives, flame retardants, synthetic reagents, and catalysts, and their efficient synthesis is an important task in organic synthesis. To synthesize novel functional organophosphorus compounds, transition-metal-catalyzed methods have been developed, which were previously considered difficult because of the strong bonding that occurs between transition metals and phosphorus. Addition reactions of triphenylphosphine and sulfonic acids to unsaturated compounds in the presence of a rhodium or palladium catalyst lead to phosphonium salts, in direct contrast to the conventional synthesis involving substitution reactions of organohalogen compounds. Rhodium and palladium complexes catalyze the cleavage of P–P bonds in diphosphines and polyphosphines and can transfer organophosphorus groups to various organic compounds. Subsequent substitution and addition reactions proceed effectively, without using a base, to provide various novel organophosphorus compounds.1 Introduction2 Transition-Metal-Catalyzed Synthesis of Phosphonium Salts by Addition Reactions of Triphenylphosphine and Sulfonic Acids3 Rhodium-Catalyzed P–P Bond Cleavage and Exchange Reactions4 Transition-Metal-Catalyzed Substitution Reactions Using Diphosphines4.1 Reactions Involving Substitution of a Phosphorus Group by P–P Bond Cleavage4.2 Related Substitution Reactions of Organophosphorus Compounds4.3 Substitution Reactions of Acid Fluorides Involving P–P Bond Cleavage of Diphosphines5 Rhodium-Catalyzed P–P Bond Cleavage and Addition Reactions6 Rhodium-Catalyzed P–P Bond Cleavage and Insertion Reactions Using Polyphosphines7 Conclusions

Transition metal-catalyzed reactions in heterocyclic chemistry

2002 ◽  
Vol 74 (8) ◽  
pp. 1327-1337 ◽  
Author(s):  
Irina P. Beletskaya
Keyword(s):  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Heterocyclic Chemistry ◽  
Substitution Reactions ◽  
Multiple Bonds ◽  
Palladium Catalyzed ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

The palladium-catalyzed substitution reactions forming carbon­carbon and carbon­element bonds, as well as nickel-catalyzed addition of E­H and E­E' bonds across multiple bonds, are considered in their application to the chemistry of heterocyclic compounds.

Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates

2015 ◽  
Vol 44 (22) ◽  
pp. 7929-7967 ◽  
Author(s):  
Nicholas A. Butt ◽  
Wanbin Zhang
Keyword(s):  
Transition Metal ◽  
Allylic Substitution ◽  
Substitution Reactions ◽  
Recent Developments ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

This review highlights recent developments in the area of transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates.

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