scholarly journals Aromaticity in catalysis: metal ligand cooperation via ligand dearomatization and rearomatization

2021 ◽  
Author(s):  
Kuo-Wei Huang ◽  
Theo P Goncalves ◽  
Indranil Dutta
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Bifunctional Catalysis ◽  
Conventional Model ◽  
Metal Catalysis ◽  
Metal Ligand

Unlike the conventional model of transition metal catalysis, ligands in metal–ligand cooperative (or bifunctional) catalysis are involved in the substrate activations. Such processes have offered unique mechanistic understandings and led...

Retaining Alkyl Nucleophile Regiofidelity in Transition-Metal-Mediated Cross-Couplings to Aryl Electrophiles

Synthesis ◽  
2018 ◽  
Vol 50 (20) ◽  
pp. 3974-3996 ◽  
Author(s):  
Josep Cornella ◽  
Matthew O’Neill
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Chemical Space ◽  
Cross Coupling ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Substantial Progress ◽  
Tertiary Alkyl ◽  
Metal Ligand

While the advent of transition-metal catalysis has undoubtedly transformed synthetic chemistry, problems persist with the introduction of secondary and tertiary alkyl nucleophiles into C(sp2) aryl electrophiles. Complications arise from the delicate organometallic intermediates typically invoked by such processes, from which competition between the desired reductive elimination event and the deleterious β-H elimination pathways can lead to undesired isomerization of the incoming nucleophile. Several methods have integrated distinct combinations of metal, ligand, nucleophile, and electrophile to provide solutions to this problem. Despite substantial progress, refinements to current protocols will facilitate the realization of complement reactivity and improved functional group tolerance. These issues have become more pronounced in the context of green chemistry and sustainable catalysis, as well as by the current necessity to develop robust, reliable cross-couplings beyond less explored C(sp2)–C(sp2) constructs. Indeed, the methods discussed herein and the elaborations thereof enable an ‘unlocking’ of accessible topologically enriched chemical space, which is envisioned to influence various domains of application.1 Introduction2 Mechanistic Considerations3 Magnesium Nucleophiles4 Zinc Nucleophiles5 Boron Nucleophiles6 Other Nucleophiles7 Tertiary Nucleophiles8 Reductive Cross-Coupling with in situ Organometallic Formation9 Conclusion

Carbon‐Sulfur Bond Constructions: From Transition‐Metal Catalysis to Sustainable Catalysis

2021 ◽  
Author(s):  
Pratheepkumar Annamalai ◽  
Ke‐Chien Liu ◽  
Satpal Singh Badsara ◽  
Chin‐Fa Lee
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Sulfur Bond

An electrochemical perspective on the roles of ligands in the merger of transition-metal catalysis and electrochemistry

2020 ◽  
Author(s):  
Ke-Yin Ye ◽  
Jun-Song Zhong ◽  
Yi Yu ◽  
Zhaojiang Shi
Keyword(s):  
Transition Metal ◽  
Organic Synthesis ◽  
Transition Metal Catalysis ◽  
Metal Catalysis

The merger of transition-metal catalysis and electrochemistry has been emerging as a very versatile and robust synthetic tool in organic synthesis. Like in their non-electrochemical variants, ligands also play crucial...

Insertion Reaction of 2-Halo-N-allylanilines with K2S Involving Trisulfur Radical Anion: Synthesis of Benzothiazole Derivatives under Transition-Metal-Free Conditions

Synthesis ◽  
2020 ◽  
Author(s):  
Yan-Wei Zhao ◽  
Shun-Yi Wang ◽  
Xin-Yu Liu ◽  
Tian Jiang ◽  
Weidong Rao
Keyword(s):  
Transition Metal ◽  
Radical Anion ◽  
Radical Cyclization ◽  
Transition Metal Catalysis ◽  
Insertion Reaction ◽  
Metal Catalysis ◽  
Metal Free ◽  
Benzothiazole Derivatives

AbstractA synthesis of benzothiazole derivatives through the reaction of 2-halo-N-allylanilines with K2S in DMF is developed. The trisulfur radical anion S3·–, which is generated in situ from K2S in DMF, initiates the reaction without transition-metal catalysis or other additives. In addition, two C–S bonds are formed and heteroaromatization of benzothiazole is triggered by radical cyclization and H-shift.

scholarly journals Enamine/Transition Metal Combined Catalysis: Catalytic Transformations Involving Organometallic Electrophilic Intermediates

2019 ◽  
Vol 377 (6) ◽  
Author(s):  
Samson Afewerki ◽  
Armando Córdova
Keyword(s):  
Transition Metal ◽  
Metal Complex ◽  
Carbonyl Compounds ◽  
Transition Metal Catalysis ◽  
Chemical Transformations ◽  
Considerable Effort ◽  
Metal Catalysis ◽  
First Report ◽  
Wide Range ◽  
Selective Chemical

AbstractThe concept of merging enamine activation catalysis with transition metal catalysis is an important strategy, which allows for selective chemical transformations not accessible without this combination. The amine catalyst activates the carbonyl compounds through the formation of a reactive nucleophilic enamine intermediate and, in parallel, the transition metal activates a wide range of functionalities such as allylic substrates through the formation of reactive electrophilic π-allyl-metal complex. Since the first report of this strategy in 2006, considerable effort has been devoted to the successful advancement of this technology. In this chapter, these findings are highlighted and discussed.

scholarly journals Tandem rhodium catalysis: exploiting sulfoxides for asymmetric transition-metal catalysis

2015 ◽  
Vol 13 (21) ◽  
pp. 5844-5847 ◽  
Author(s):  
K. G. M. Kou ◽  
V. M. Dong
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Rhodium Catalysis ◽  
Alkene Hydrogenation

Sulfoxides are uncommon substrates for transition-metal catalysis due to their propensity to inhibit catalyst turnover. We have developed the first DKR of racemic allylic sulfoxides where rhodium catalyzed both sulfoxide epimerization and alkene hydrogenation.

Transition metal catalysis and nucleophilic fluorination

2012 ◽  
Vol 48 (24) ◽  
pp. 2929 ◽  
Author(s):  
Charlotte Hollingworth ◽  
Véronique Gouverneur
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Nucleophilic Fluorination
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