Triflic Anhydride (Tf2O)-Activated Transformation of Amides, Sulfoxides and Phosphorus Oxides via Nucleophilic Trapping

Synthesis ◽  
2021 ◽  
Author(s):  
Hai Huang ◽  
Jun Yong Kang
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Phosphorus Oxide ◽  
Synthetic Organic Chemistry ◽  
The Past ◽  
Mechanistic Pathway ◽  
Trifluoromethanesulfonic Anhydride ◽  
Wide Range ◽  
Electrophilic Activation ◽  
Nucleophilic Trapping

Trifluoromethanesulfonic anhydride (Tf2O) has found a wide range of applications in synthetic organic chemistry as a strong electrophilic activator leading to the transient generation of a triflate intermediate. This versatile triflate intermediate undergoes nucleophilic trapping with diverse nucleophiles to yield novel compounds. In this review, we describe the features and applications of triflic anhydride in organic synthesis reported in the past decade, especially in amide, sulfoxide, and phosphorus oxide chemistry through electrophilic activation. A plausible mechanistic pathway of each important reaction is also discussed.

scholarly journals Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

2018 ◽  
Vol 14 ◽  
pp. 1778-1805 ◽  
Author(s):  
Fateh V Singh ◽  
Priyanka B Kole ◽  
Saeesh R Mangaonkar ◽  
Samata E Shetgaonkar
Keyword(s):  
Organic Chemistry ◽  
Heavy Metals ◽  
Natural Product ◽  
Organic Synthesis ◽  
Stereoselective Synthesis ◽  
Natural Product Synthesis ◽  
Hypervalent Iodine ◽  
Toxic Heavy Metals ◽  
Synthetic Organic Chemistry ◽  
The Past

Hypervalent iodine reagents have been developed as highly valuable reagents in synthetic organic chemistry during the past few decades. These reagents have been identified as key replacements of various toxic heavy metals in organic synthesis. Various synthetically and biologically important scaffolds have been developed using hypervalent iodine reagents either in stoichiometric or catalytic amounts. In addition, hypervalent iodine reagents have been employed for the synthesis of spirocyclic scaffolds via dearomatization processes. In this review, various approaches for the synthesis of spirocyclic scaffolds using hypervalent iodine reagents are covered including their stereoselective synthesis. Additionally, the applications of these reagents in natural product synthesis are also covered.

scholarly journals Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 249
Author(s):  
Raquel G. Soengas ◽  
Humberto Rodríguez-Solla
Keyword(s):  
Organic Chemistry ◽  
Natural Products ◽  
Functional Group ◽  
Biological Activities ◽  
Synthetic Methods ◽  
Bond Forming ◽  
Drug Candidates ◽  
The Past ◽  
Wide Range

The 1,3-butadiene motif is widely found in many natural products and drug candidates with relevant biological activities. Moreover, dienes are important targets for synthetic chemists, due to their ability to give access to a wide range of functional group transformations, including a broad range of C-C bond-forming processes. Therefore, the stereoselective preparation of dienes have attracted much attention over the past decades, and the search for new synthetic protocols continues unabated. The aim of this review is to give an overview of the diverse methodologies that have emerged in the last decade, with a focus on the synthetic processes that meet the requirements of efficiency and sustainability of modern organic chemistry.

Illuminating a Path for Organic Synthesis Towards Sustainability. No One Said It Would Be Easy…

Synlett ◽  
2021 ◽  
Author(s):  
Bruce H. Lipshutz
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Reaction Medium ◽  
Base Metals ◽  
Bottom Line ◽  
Reactive Metal ◽  
Metal Chemistry ◽  
The Past ◽  
Environmentally Responsible ◽  
Petroleum Reserves

AbstractA personalized account is presented describing some of the stories behind the scenes in efforts to convert organic chemistry into a more sustainable discipline. These are part of a group ‘crusade’ started almost 15 years ago aimed at providing technologies illustrative of how key reactions used today can be ‘faster, better, cheaper’ when run in recyclable water. Hence, the option now exists to do organic synthesis in a far more environmentally responsible fashion. By contrast, most of organic chemistry developed over the past 200 years that relies on organic solvents continues to generate enormous amounts of pollution, while depleting finite petroleum reserves and our supplies of many precious and base metals. Making the switch to water, Nature’s chosen reaction medium, akin to that in which bio-catalysis is typically performed, is inevitable.1 The Story Begins: A Different Type of Prejudice2 Are We up to the Challenge? Too Late Now…3 ‘Impossible’ Reactive Metal Chemistry in Water4 Didn’t I Once Say: ‘It’s All about the Ligand’?5 What Happens When Our Supply of Palladium Runs Out?6 What Are the Implications from These Tales for Today and Tomorrow?7 What Is the ‘Broader Impact’ of This Work?8 The Bottom Line…

scholarly journals Application of Complexes of Group 13 Elements in Synthetic Organic Chemistry for Activation of Carbonyl Compounds

Vestnik RFFI ◽  
2019 ◽  
pp. 113-140
Author(s):  
Roman A. Novikov ◽  
Yury V. Tomilov
Keyword(s):  
Organic Chemistry ◽  
Coordination Chemistry ◽  
Organic Synthesis ◽  
Carbonyl Compounds ◽  
Group 13 ◽  
New Era ◽  
Synthetic Organic Chemistry ◽  
Main Emphasis ◽  
New Compounds

The main aspects of modern organic chemistry of the Group 13 elements – aluminum (Al), gallium (Ga), indium (In), and thallium (Tl) – are considered. Herewith, the main emphasis is placed on their use for the various carbonyl compounds activation in organic synthesis and reactions, which are specific for these elements. The 21th century marked a new era in the development of chemistry of the Group 13 elements; it is connected with the discovery of surprising and unexpected reactions and new compounds (primarily in the area of organic and coordination chemistry), defining various fields of these elements application.

scholarly journals Copper-boryl mediated organic synthesis

2018 ◽  
Vol 47 (19) ◽  
pp. 7477-7494 ◽  
Author(s):  
David Hemming ◽  
Russell Fritzemeier ◽  
Stephen A. Westcott ◽  
Webster L. Santos ◽  
Patrick G. Steel
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Synthetic Organic Chemistry

The diverse applications of copper-catalyzed borylation, which has become an essential strategy in modern synthetic organic chemistry, are reviewed and illustrated.

scholarly journals Supported Metal Catalysts for the Synthesis of N-Heterocycles

Catalysts ◽  
2022 ◽  
Vol 12 (1) ◽  
pp. 68
Author(s):  
Laura Antonella Aronica ◽  
Gianluigi Albano
Keyword(s):  
Organic Chemistry ◽  
Systematic Approach ◽  
Metal Catalysts ◽  
Supported Metal Catalysts ◽  
The Past ◽  
Wide Range ◽  
Organic Matrices ◽  
Metal Catalyzed ◽  
Critical Overview ◽  
Supported Metal

Nitrogen-containing heterocycles are important scaffolds for a large number of compounds with biological, pharmaceutical, industrial and optoelectronic applications. A wide range of different methodologies for the preparation of N-heterocycles are based on metal-catalyzed cyclization of suitable substrates. Due to the growing interest in Green Chemistry criteria over the past two decades, the use of supported metal catalysts in the preparation of N-heterocycles has become a central topic in Organic Chemistry. Here we will give a critical overview of all the solid supported metal catalysts applied in the synthesis of N-heterocycles, following a systematic approach as a function of the type of support: (i) metal catalysts supported on inorganic matrices; (ii) metal catalysts supported on organic matrices; (iii) metal catalysts supported on hybrid inorganic-organic matrices. In particular, we will try to emphasize the effective heterogeneity and recyclability of the described metal catalysts, specifying which studies were carried out in order to evaluate these aspects.

scholarly journals Electrocatalysis as an enabling technology for organic synthesis

2021 ◽  
Author(s):  
Luiz F. T. Novaes ◽  
Jinjian Liu ◽  
Yifan Shen ◽  
Lingxiang Lu ◽  
Jonathan M. Meinhardt ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Enabling Technology ◽  
Synthetic Organic Chemistry

Electrochemistry has recently gained increased attention as a versatile strategy for achieving challenging transformations at the forefront of synthetic organic chemistry.

scholarly journals N-Heterocyclic carbene/Brønsted acid cooperative catalysis as a powerful tool in organic synthesis

2012 ◽  
Vol 8 ◽  
pp. 398-402 ◽  
Author(s):  
Rob De Vreese ◽  
Matthias D’hooghe
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Stereoselective Synthesis ◽  
Heterocyclic Carbenes ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Heterocyclic Chemistry ◽  
The Past ◽  
Cooperative Catalysis ◽  
Brönsted Acid

The interplay between metals and N-heterocyclic carbenes (NHCs) has provided a window of opportunities for the development of novel catalytic strategies within the past few years. The recent successful combination of Brønsted acids with NHCs has added a new dimension to the field of cooperative catalysis, enabling the stereoselective synthesis of functionalized pyrrolidin-2-ones as valuable scaffolds in heterocyclic chemistry. This Commentary will briefly highlight the concept of N-heterocyclic carbene/Brønsted acid cooperative catalysis as a new and powerful methodology in organic chemistry.

Thieme–IUPAC Prize 2016 Call for Nominations

2015 ◽  
Vol 37 (5-6) ◽  
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
International Union ◽  
Applied Chemistry ◽  
Synthetic Organic Chemistry ◽  
International Conference

Thieme Chemistry, IUPAC, and the Editors of SYNTHESIS, SYNLETT, SYNFACTS, and Science of Synthesis announce the Thieme–IUPAC Prize for 2016. This award is presented every two years on the occasion of the International Union of Pure and Applied Chemistry – International Conference on Organic Synthesis (IUPAC–ICOS). The 2016 ICOS will be held at IIT Bombay in Mumbai, India, 11-16 December 2016. The prize is awarded to a scientist under 40 years of age whose research has had a major impact in synthetic organic chemistry.

scholarly journals Rhodococcus as A Versatile Biocatalyst in Organic Synthesis

2019 ◽  
Vol 20 (19) ◽  
pp. 4787 ◽  
Author(s):  
Busch ◽  
Hagedoorn ◽  
Hanefeld
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Specific Enzyme ◽  
Close Attention ◽  
Comprehensive Overview ◽  
Whole Cell ◽  
Synthetic Organic Chemistry ◽  
Utilization Potential ◽  
Enzyme Class

The application of purified enzymes as well as whole-cell biocatalysts in synthetic organic chemistry is becoming more and more popular, and both academia and industry are keen on finding and developing novel enzymes capable of performing otherwise impossible or challenging reactions. The diverse genus Rhodococcus offers a multitude of promising enzymes, which therefore makes it one of the key bacterial hosts in many areas of research. This review focused on the broad utilization potential of the genus Rhodococcus in organic chemistry, thereby particularly highlighting the specific enzyme classes exploited and the reactions they catalyze. Additionally, close attention was paid to the substrate scope that each enzyme class covers. Overall, a comprehensive overview of the applicability of the genus Rhodococcus is provided, which puts this versatile microorganism in the spotlight of further research.

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