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…

Ionic Liquids for the Synthesis of Five-Membered N,N-, N,N,N- and N,N,N,NHeterocycles

2019 ◽  
Vol 23 (11) ◽  
pp. 1214-1238 ◽  
Author(s):  
Navjeet Kaur ◽  
Pranshu Bhardwaj ◽  
Meenu Devi ◽  
Yamini Verma ◽  
Neha Ahlawat ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Reaction Medium ◽  
Environmental Issues ◽  
Organic Reaction ◽  
Environment Friendly ◽  
The Past ◽  
Area Of Interest ◽  
Major Subject

Due to special properties of ILs (Ionic Liquids) like their wide liquid range, good solvating ability, negligible vapour pressure, non-inflammability, environment friendly medium, high thermal stability, easy recycling and rate promoters etc. they are used in organic synthesis. The investigation for the replacement of organic solvents in organic synthesis is a growing area of interest due to increasing environmental issues. Therefore, ionic liquids have attracted the attention of chemists and act as a catalyst and reaction medium in organic reaction with high activity. There is no doubt that ionic liquids have become a major subject of study for modern chemistry. In comparison to traditional processes the use of ionic liquids resulted in improved, complimentary or alternative selectivities in organic synthesis. The present manuscript reported the synthesis of multiple nitrogen containing five-membered heterocyclic compounds using ionic liquids. This review covered interesting discoveries in the past few years.

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 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.

scholarly journals Alkene Difunctionalization Using Hypervalent Iodine Reagents: Progress and Developments in the Past Ten Years

Molecules ◽  
2019 ◽  
Vol 24 (14) ◽  
pp. 2634 ◽  
Author(s):  
Lee ◽  
Choi ◽  
Hong
Keyword(s):  
Organic Chemistry ◽  
Transition Metal ◽  
Hypervalent Iodine ◽  
Transition Metal Chemistry ◽  
Metal Chemistry ◽  
The Past ◽  
Catalytic Asymmetric ◽  
Alkene Difunctionalization

Hypervalent iodine reagents are of considerable relevance in organic chemistry as they can provide a complementary reaction strategy to the use of traditional transition metal chemistry. Over the past two decades, there have been an increasing number of applications including stoichiometric oxidation and catalytic asymmetric variations. This review outlines the main advances in the past 10 years in regard to alkene heterofunctionalization chemistry using achiral and chiral hypervalent iodine reagents and catalysts.

Boron–nitrogen doped carbon scaffolding: organic chemistry, self-assembly and materials applications of borazine and its derivatives

2015 ◽  
Vol 51 (83) ◽  
pp. 15222-15236 ◽  
Author(s):  
Davide Bonifazi ◽  
Francesco Fasano ◽  
M. Mercedes Lorenzo-Garcia ◽  
Davide Marinelli ◽  
Hamid Oubaha ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Self Assembly ◽  
Feature Article ◽  
Nitrogen Doped ◽  
The Past ◽  
Recent Developments ◽  
Nitrogen Doped Carbon ◽  
Boron Nitrogen

In this feature article we describe the past and recent developments in the organic synthesis and functionalisation of borazine, the isostructural inorganic analogue of benzene.

scholarly journals FUNdamental Developments in the Undergraduate Organic Chemistry Laboratory

2020 ◽  
Author(s):  
Monika R. Snowdon
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Undergraduate Students ◽  
Learning Experience ◽  
Chemistry Laboratory ◽  
The Past ◽  
Interesting Topic ◽  
Improved Learning ◽  
Organic Chemistry Laboratory

The undergraduate lab for organic chemistry varies from campus to campus. However, the consensus from students does less so. In general, organic chemistry is one of the most daunting courses for science undergraduate students, and the content presented in the corresponding laboratories of these courses can be equally difficult. There has been a shift towards modifying the content of the organic chemistry lab to make it an improved learning experience for the students, such that schools are graduating better chemists, as ultimately, the students are retaining the skills and information more efficiently. This study reviews some of the past decade's improvements towards modifying the organic chemistry undergraduate lab experience to make organic synthesis a more engaging and interesting topic for students.

Negotiating Tripartite Philosophy (Strategy–tactics–technique)

2019 ◽  
Vol 1 (1) ◽  
pp. 53
Author(s):  
Hazem Hamad Mousa Al Janabi
Keyword(s):  
Bottom Line ◽  
Negotiation Strategy ◽  
The Third ◽  
The Past

Tripartite Negotiating philosophy: (strategy - tactics - technique) At the beginning , the research consists of four sections as follows: The first axis titled: "what negotiation", and the second axis: "philosophy of negotiation," The third axis titled: "negotiation strategy". Down to the fourth axis which included titled: "negotiating tactic", Sajama with the past and as a supplement came fifth axis titled: "negotiating technique", to be the bottom line in the form of a set of conclusions. Negotiation consists of a base triple hierarchical strategy - tactics - technique. The philosophy of negotiating interactive basis of rationality. Negotiable three parties are the position and the case and the parties involved. Is the process of negotiating strategic recruitment capacity and capabilities to achieve the desired goal of the crisis prematurely. Negotiating tactic is the process of hiring capacity and capabilities to achieve the desired goal at the negotiating table. •The technique is the process of negotiating employment capacity and capabilities to achieve the desired goal at the negotiating table to contain thesudden things check response and renewed flexibility.

The molecular diversity of 1,8-diaminonaphthalene in organic chemistry

2020 ◽  
Vol 23 ◽  
Author(s):  
Ghodsi Mohammadi Ziarani ◽  
Fatemeh Mohajer ◽  
Suraj N. Mali
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Molecular Diversity ◽  
Organic Reactions ◽  
Recent Application ◽  
Organic Structure

: 1,8-diaminonaphthalene (1,8-DAN) with special organic structure was applied in organic synthesis to provide efficient complex scaffolds, through the two or four-component fashion. This review highlights its recent application in organic reactions under different conditions and heterogynous catalysts to produce various molecules, which were used as medicines, sensors, and dyes.

Metal and Non-Metal Catalysts in the Synthesis of Five-Membered S-Heterocycles

2019 ◽  
Vol 16 (2) ◽  
pp. 258-275 ◽  
Author(s):  
Navjeet Kaur
Keyword(s):  
Organic Synthesis ◽  
Biological Activities ◽  
Reaction Times ◽  
Research Field ◽  
Environmentally Benign ◽  
Metal Catalyst ◽  
Efficient Synthesis ◽  
Heterocyclic Molecules ◽  
The Past ◽  
Harsh Conditions

Background:A wide variety of biological activities are exhibited by N, O and S containing heterocycles and recently, many reports appeared for the synthesis of these heterocycles. The synthesis of heterocycles with the help of metal and non-metal catalyst has become a highly rewarding and important method in organic synthesis. This review article concentrated on the synthesis of S-heterocylces in the presence of metal and non-metal catalyst. The synthesis of five-membered S-heterocycles is described here.Objective:There is a need for the development of rapid, efficient and versatile strategy for the synthesis of heterocyclic rings. Metal, non-metal and organocatalysis involving methods have gained prominence because traditional conditions have disadvantages such as long reaction times, harsh conditions and limited substrate scope.Conclusion:The metal-, non-metal-, and organocatalyst assisted organic synthesis is a highly dynamic research field. For ßthe chemoselective and efficient synthesis of heterocyclic molecules, this protocol has emerged as a powerful route. Various methodologies in the past few years have been pointed out to pursue more sustainable, efficient and environmentally benign procedures and products. Among these processes, the development of new protocols (catalysis), which avoided the use of toxic reagents, are the focus of intense research.

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