scholarly journals Nickel/brønsted acid dual-catalyzed regio- and enantioselective hydrophosphinylation of 1,3-dienes: access to chiral allylic phosphine oxides

2022 ◽  
Author(s):  
Jiao Long ◽  
Yuqiang Li ◽  
Weining Zhao ◽  
Guoyin Yin
Keyword(s):  
Asymmetric Catalysis ◽  
Organophosphorus Compounds ◽  
Synthetic Methods ◽  
Bioactive Molecules ◽  
Phosphine Oxides ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid

While chiral allylic organophosphorus compounds are widely utilized in asymmetric catalysis and bioactive molecules, their synthetic methods are still very limited. We report the development of an asymmetric nickel/brønsted acid...

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

scholarly journals Brønsted Acid Promoted Reduction of Tertiary Phosphine Oxides

2017 ◽  
Vol 643 (14) ◽  
pp. 916-921 ◽  
Author(s):  
Tetiana Krachko ◽  
Volodymyr Lyaskovskyy ◽  
Martin Lutz ◽  
Koop Lammertsma ◽  
J. Chris Slootweg
Keyword(s):  
Phosphine Oxides ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Tertiary Phosphine ◽  
Brönsted Acid

Cover Picture: Brønsted Acid Promoted Reduction of Tertiary Phosphine Oxides (Z. Anorg. Allg. Chem. 14/2017)

2017 ◽  
Vol 643 (14) ◽  
pp. 877-877
Author(s):  
Tetiana Krachko ◽  
Volodymyr Lyaskovskyy ◽  
Martin Lutz ◽  
Koop Lammertsma ◽  
J. Chris Slootweg
Keyword(s):  
Phosphine Oxides ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Tertiary Phosphine ◽  
Brönsted Acid

Catalytic Lewis and Brønsted acid syn-diastereoselective benzylic substitutions of α-hydroxy-β-nitro- and α-hydroxy-β-azido-alkyl arenes

2020 ◽  
Vol 98 (6) ◽  
pp. 292-306
Author(s):  
Raphaël Hensienne ◽  
Jean-Philippe Cusson ◽  
Étienne Chénard ◽  
Stephen Hanessian
Keyword(s):  
Transition State ◽  
Asymmetric Catalysis ◽  
Amino Alcohol ◽  
Chiral Ligands ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Benzylic Alcohols ◽  
New Synthesis ◽  
Brönsted Acid ◽  
State Models

A series of alkyl and alkenyl p-methoxy arenes containing α,β-disubstituted diamino and amino alcohol groups were synthesized from β-nitro and β-azido benzylic alcohols in the presence of AuCl3 as catalyst. The formation of predominantly syn-disubstituted products were rationalized on the basis of mechanistic considerations and transition state models relying on A1,3-allylic strain. The products could have utility in the design of medicinally relevant compounds and as chiral ligands for asymmetric catalysis. A new synthesis of (+)-sertraline (Zoloft) was achieved.

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