Dual Catalysis: A Combined Enantioselective Brønsted Acid and Metal-Catalyzed Reaction—Metal Catalysis with Chiral Counterions

2007 ◽  
Vol 46 (36) ◽  
pp. 6903-6906 ◽  
Author(s):  
Magnus Rueping ◽  
Andrey P. Antonchick ◽  
Claus Brinkmann
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Metal Catalysis ◽  
Brönsted Acid ◽  
Dual Catalysis ◽  
Metal Catalyzed

Direct Catalytic Asymmetric Mannich-Type Reactions of γ-Butenolides: Effectiveness of Brønsted Acid in Chiral Metal Catalysis

2008 ◽  
Vol 10 (11) ◽  
pp. 2319-2322 ◽  
Author(s):  
Akitake Yamaguchi ◽  
Shigeki Matsunaga ◽  
Masakatsu Shibasaki
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Metal Catalysis ◽  
Brönsted Acid ◽  
Catalytic Asymmetric

Amide Synthesis by Transamidation of Primary Carboxamides

Synthesis ◽  
2020 ◽  
Vol 52 (21) ◽  
pp. 3231-3242
Author(s):  
Sylvain Laclef ◽  
Maria Kolympadi Marković ◽  
Dean Marković
Keyword(s):  
Synthetic Methods ◽  
Amide Bond ◽  
Industrial Chemistry ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Atom Economy ◽  
Bond Forming ◽  
Effective Strategies ◽  
Brönsted Acid ◽  
Metal Catalyzed

The amide functionality is one of the most important and widely used groups in nature and in medicinal and industrial chemistry. Because of its importance and as the actual synthetic methods suffer from major drawbacks, such as the use of a stoichiometric amount of an activating agent, epimerization and low atom economy, the development of new and efficient amide bond forming reactions is needed. A number of greener and more effective strategies have been studied and developed. The transamidation of primary amides is particularly attractive in terms of atom economy and as ammonia is the single byproduct. This review summarizes the advancements in metal-catalyzed and organocatalyzed transamidation methods. Lewis and Brønsted acid transamidation catalysts are reviewed as a separate group. The activation of primary amides by promoter, as well as catalyst- and promoter-free protocols, are also described. The proposed mechanisms and key intermediates of the depicted transamidation reactions are shown.1 Introduction2 Metal-Catalyzed Transamidations3 Organocatalyzed Transamidations4 Lewis and Brønsted Acid Catalysis5 Promoted Transamidation of Primary Amides6 Catalyst- and Promoter-Free Protocols7 Conclusion

Facile synthesis of N-aryl phenothiazines and phenoxazines via Brønsted acid catalyzed C−H amination of arenes

2022 ◽  
Author(s):  
Wang Xia ◽  
Zi-An Zhou ◽  
Jie Lv ◽  
Shao-Hua Xiang ◽  
Yong-Bin Wang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Facile Synthesis ◽  
Synthetic Strategy ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

N-aryl phenothiazines and phenoxazines are of significant importance in various disciplines throughout academia and industry. Conventional synthetic strategy for the construction of these structures centers on transition-metal-catalyzed cross-coupling of aryl...

Claisen Rearrangement Triggered by Brønsted Acid Catalyzed Alkyne Alkoxylation

Synlett ◽  
2022 ◽  
Author(s):  
Long Li ◽  
Long-Wu Ye ◽  
Yao-Hong Yan
Keyword(s):  
Claisen Rearrangement ◽  
High Efficiency ◽  
Rapid Development ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Diverse Range ◽  
Claisen Rearrangements ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
Metal Catalyzed

AbstractOver the past two decades, catalytic alkyne alkoxylation-initiated Claisen rearrangement has proven to be a practical and powerful strategy for the rapid assembly of a diverse range of structurally complex molecules. The rapid development of Claisen rearrangements triggered by transition-metal-catalyzed alkyne alkoxylation has shown great potential in the formation of carbon–carbon bonds in an atom-economic and mild way. However, metal-free alkyne alkoxylation-triggered Claisen rearrangement has seldom been exploited. Recently, Brønsted acids such as HNTf2 and HOTf have been shown to be powerful activators that promote catalytic alkyne alkoxylation/Claisen rearrangement, leading to the concise and flexible synthesis of valuable compounds with high efficiency and atom economy. Recent advances on the Brønsted acid catalyzed alkyne alkoxylation/Claisen rearrangement are introduced in this Account, in which both intramolecular and intermolecular tandem reactions are discussed.

The electrophilic aromatic substitution approach to C–H silylation and C–H borylation

2018 ◽  
Vol 90 (4) ◽  
pp. 723-731 ◽  
Author(s):  
Susanne Bähr ◽  
Martin Oestreich
Keyword(s):  
Transition Metal ◽  
Lewis Acid ◽  
Electrophilic Aromatic Substitution ◽  
Bronsted Acid ◽  
Aromatic Substitution ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

AbstractSeveral approaches toward electrophilic C–H silylation of electron-rich arenes are discussed, comprising transition-metal-catalyzed processes as well as Lewis-acid- and Brønsted-acid-induced protocols. These methods differ in the catalytic generation of the silicon electrophile but share proton removal in form of dihydrogen. With slight modifications, these methods are often also applicable to the related electrophilic C–H borylation.

scholarly journals Hydroamination reactions by metal triflates: Brønsted acid vs. metal catalysis?

2010 ◽  
Vol 39 (5) ◽  
pp. 1171-1175 ◽  
Author(s):  
Jason G. Taylor ◽  
Luis A. Adrio ◽  
King Kuok (Mimi) Hii
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Metal Catalysis ◽  
Brönsted Acid ◽  
Metal Triflates
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