Alkyne–phosphinoalkyne coupling reactions on mixed-metal tungsten–cobalt centres; P–C(alkyne) bond cleavage versus P–C(alkyne) bond preservation

2001 ◽  
pp. 1269-1277 ◽  
Author(s):  
John E. Davies ◽  
Martin J. Mays ◽  
Paul R. Raithby ◽  
Koshala Sarveswaran ◽  
Gregory A. Solan
Keyword(s):  
Bond Cleavage ◽  
Coupling Reactions ◽  
Mixed Metal

Double C–H Activation for the C–C bond Formation Reactions

2018 ◽  
Vol 15 (7) ◽  
pp. 882-903 ◽  
Author(s):  
Jialin Liu ◽  
Xiaoyu Xiong ◽  
Jie Chen ◽  
Yuntao Wang ◽  
Ranran Zhu ◽  
...  
Keyword(s):  
Molecular Design ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Hypervalent Iodine ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Direct Functionalization ◽  
Catalyzed Reactions ◽  
Medium Ring ◽  
Bond Formation Reactions

Background: Among the numerous bond-forming patterns, C–C bond formation is one of the most useful tools for building molecules for the chemical industry as well as life sciences. Recently, one of the most challenging topics is the study of the direct coupling reactions via multiple C–H bond cleavage/activation processes. A number of excellent reviews on modern C–H direct functionalization have been reported by Bergman, Bercaw, Yu and others in recent years. Among the large number of available methodologies, Pdcatalyzed reactions and hypervalent iodine reagent mediated reactions represent the most popular metal and non-metal involved transformations. However, the comprehensive summary of the comparison of metal and non-metal mediated transformations is still not available. Objective: The review focuses on comparing these two types of reactions (Pd-catalyzed reactions and hypervalent iodine reagent mediated reactions) based on the ways of forming new C–C bonds, as well as the scope and limitations on the demonstration of their synthetic applications. Conclusion: Comparing the Pd-catalyzed strategies and hypervalent iodine reagent mediated methodologies for the direct C–C bond formation from activation of C-H bonds, we clearly noticed that both strategies are powerful tools for directly obtaining the corresponding pruducts. On one hand, the hypervalent iodine reagents mediated reactions are normally under mild conditions and give the molecular diversity without the presence of transition-metal, while the Pd-catalyzed approaches have a broader scope for the wide synthetic applications. On the other hand, unlike Pd-catalyzed C-C bond formation reactions, the study towards hypervalent iodine reagent mediated methodology mainly focused on the stoichiometric amount of hypervalent iodine reagent, while few catalytic reactions have been reported. Meanwhile, hypervalent iodine strategy has been proved to be more efficient in intramolecular medium-ring construction, while there are less successful examples on C(sp3)–C(sp3) bond formation. In summary, we have demonstrated a number of selected approaches for the formation of a new C–C bond under the utilization of Pd-catalyzed reaction conditions or hyperiodine reagents. The direct activations of sp2 or sp3 hybridized C–H bonds are believed to be important strategies for the future molecular design as well as useful chemical entity synthesis.

Palladium-Catalyzed Carbonylative Coupling Reactions of N ,N -Bis(methanesulfonyl)amides through C-N Bond Cleavage

2018 ◽  
Vol 2018 (41) ◽  
pp. 5717-5724 ◽  
Author(s):  
Minkyung Lim ◽  
Hyeji Kim ◽  
Jaeyoung Ban ◽  
Junghan Son ◽  
Jae Kyun Lee ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Coupling Reactions ◽  
Palladium Catalyzed

Recent Advances in the Coupling Reactions of Arylhydrazine via C—N Bond Cleavage

2016 ◽  
Vol 36 (8) ◽  
pp. 1790 ◽  
Author(s):  
Jinbiao Liu ◽  
Sitian Yuan ◽  
Xixi Song ◽  
Guanyinsheng Qiu
Keyword(s):  
Bond Cleavage ◽  
Coupling Reactions ◽  
Recent Advances

scholarly journals Well-Defined Pre-Catalysts in Amide and Ester Bond Activation

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 215 ◽  
Author(s):  
Sandeep R. Vemula ◽  
Michael R. Chhoun ◽  
Gregory R. Cook
Keyword(s):  
Transition Metal ◽  
Bond Activation ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
Ester Bond ◽  
Coupling Reactions ◽  
Catalytic Systems ◽  
Design And Synthesis ◽  
Cross Coupling Reactions ◽  
Made In

Over the past few decades, transition metal catalysis has witnessed a rapid and extensive development. The discovery and development of cross-coupling reactions is considered to be one of the most important advancements in the field of organic synthesis. The design and synthesis of well-defined and bench-stable transition metal pre-catalysts provide a significant improvement over the current catalytic systems in cross-coupling reactions, avoiding excess use of expensive ligands and harsh conditions for the synthesis of pharmaceuticals, agrochemicals and materials. Among various well-defined pre-catalysts, the use of Pd(II)-NHC, particularly, provided new avenues to expand the scope of cross-coupling reactions incorporating unreactive electrophiles, such as amides and esters. The strong σ-donation and tunable steric bulk of NHC ligands in Pd-NHC complexes facilitate oxidative addition and reductive elimination steps enabling the cross-coupling of broad range of amides and esters using facile conditions contrary to the arduous conditions employed under traditional catalytic conditions. Owing to the favorable catalytic activity of Pd-NHC catalysts, a tremendous progress was made in their utilization for cross-coupling reactions via selective acyl C–X (X=N, O) bond cleavage. This review highlights the recent advances made in the utilization of well-defined pre-catalysts for C–C and C–N bond forming reactions via selective amide and ester bond cleavage.

Vapor-phase methanol and ethanol coupling reactions on CuMgAl mixed metal oxides

2013 ◽  
Vol 455 ◽  
pp. 234-246 ◽  
Author(s):  
Juan J. Bravo-Suárez ◽  
Bala Subramaniam ◽  
Raghunath V. Chaudhari
Keyword(s):  
Metal Oxides ◽  
Vapor Phase ◽  
Mixed Metal Oxides ◽  
Coupling Reactions ◽  
Mixed Metal

Phosphorus–sulfur bond cleavage at a mixed-metal centre; reaction of [(OC)3Co(µ-PHCCH)Mo(CO)2(η5-C5H5)] with PPh2(SPh)

1994 ◽  
pp. 3607-3614 ◽  
Author(s):  
Scott L. Ingham ◽  
Martin J. Mays ◽  
Paul R. Raithby ◽  
Gregory A. Solan ◽  
Bharat V. Sundavadra ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Metal Centre ◽  
Mixed Metal ◽  
Sulfur Bond

scholarly journals Palladium catalyzed Suzuki cross-coupling of benzyltrimethylammonium salts via C–N bond cleavage

RSC Advances ◽  
2017 ◽  
Vol 7 (26) ◽  
pp. 15805-15808 ◽  
Author(s):  
Tao Wang ◽  
Shuwu Yang ◽  
Silin Xu ◽  
Chunyu Han ◽  
Ge Guo ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Efficient Approach ◽  
Highly Efficient ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
The Way

A Pd catalyzed Suzuki cross-coupling of a benzyltrimethylammonium salt is described. This reaction offers a highly efficient approach to diarylmethanes and also paves the way for the application of benzyltrimethylammonium salts in Pd catalyzed cross-coupling reactions.

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