Advances in the Mitsunobu Reaction: An Excellent Organic Protocol with Versatile Applications

2019 ◽  
Vol 16 (2) ◽  
pp. 127-140 ◽  
Author(s):  
Sharad Kumar Panday
Keyword(s):  
Organic Synthesis ◽  
Turning Point ◽  
Mitsunobu Reaction ◽  
Present Review ◽  
Secondary Alcohols ◽  
Rapid Progress ◽  
Reaction Conditions ◽  
Recent Advances ◽  
Basic Objective ◽  
Made In

The beginning of 1970’s may well be regarded as turning point in the area of organic synthesis when an efficient and straight forward strategy for the reaction of primary and/or secondary alcohols with variety of nucleophiles in the presence of triphenylphosphine and azodicarboxylate reagent was discovered by O. Mitsunobu and since then rapid progress has been made in understanding and applying the Mitsunobu reaction for various derivatization reactions. Due to versatile applications and mild reaction conditions associated with the said strategy, the Mitsunobu reaction has received much attention in the last almost fifty years and has been well reported. The basic objective of this review is to pay attention on the recent advances and applications of the Mitsunobu reaction particularly in last decade. The attention has also been paid to describe various modifications which have been explored in the traditional Mitsunobu reaction by substituting P (III) reagents or azodicarboxylate reagents with other suitable reagents or else using an organocatalyst with the objective to improve upon the traditional Mitsunobu reaction. In the present review we wish to report the major advancements achieved in last few years which are likely to be beneficial for the researchers across the globe.

Ligand-Driven Advances in Iridium Catalyzed sp3 C-H Borylation: 2,2’-Dipyridylarylmethane

Synlett ◽  
2020 ◽  
Author(s):  
Margaret R Jones ◽  
Nathan D. Schley
Keyword(s):  
Recent Work ◽  
Organic Synthesis ◽  
Functional Group ◽  
Reaction Conditions ◽  
Recent Advances ◽  
Additional Ligand ◽  
Limited Application ◽  
Hydrocarbon Substrates ◽  
Phenanthroline Ligands

The field of catalytic C-H borylation has grown considerably since its founding, providing a means for the preparation of synthetically versatile organoborane products. While sp2 C-H borylation methods have found widespread and practical use in organic synthesis, the analogous sp3 C-H borylation reaction remains challenging and has seen limited application. Existing catalysts are often hindered by incomplete consumption of the diboron reagent, poor functional group tolerance, harsh reaction conditions, and the need for excess or neat substrate. These challenges acutely affect C-H borylation chemistry of unactivated hydrocarbon substrates, which has lagged in comparison to methods for the C-H borylation of activated compounds. Herein we discuss recent advances in sp3 C-H borylation of undirected substrates in the context of two particular challenges: (1) utilization of the diboron reagent and (2) the need for excess or neat substrate. Our recent work on the application of dipyridylarylmethane ligands in sp3 C-H borylation has allowed us to make contributions in this space and has presented an additional ligand scaffold to supplement traditional phenanthroline ligands.

scholarly journals Recent Advances in Palladium-Catalyzed Isocyanide Insertions

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 4906
Author(s):  
Jurriën W. Collet ◽  
Thomas R. Roose ◽  
Bram Weijers ◽  
Bert U. W. Maes ◽  
Eelco Ruijter ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Building Blocks ◽  
Insertion Reactions ◽  
Chemical Reagents ◽  
The Past ◽  
Recent Advances ◽  
Recent Developments ◽  
Palladium Catalyzed ◽  
Made In ◽  
Rapid Incorporation

Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function as a CO-substitute in palladium-catalyzed cross couplings. Over the past decades, isocyanides have emerged as practical and versatile C1 building blocks, whose inherent N-substitution allows for the rapid incorporation of nitrogeneous fragments in a wide variety of products. Recent developments in palladium catalyzed isocyanide insertion reactions have significantly expanded the scope and applicability of these imidoylative cross-couplings. This review highlights the advances made in this field over the past eight years.

1.9 Oxygen-Centered Radicals

2021 ◽  
Author(s):  
J. Zhang ◽  
D. Liu ◽  
Y. Chen
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Organic Synthesis ◽  
Reactive Intermediates ◽  
Radical Addition ◽  
Hydrogen Atom Transfer ◽  
Reaction Conditions ◽  
Recent Advances ◽  
Carbon Carbon Bonds ◽  
Induced Reaction

AbstractOxygen-centered radicals (R1O•) are reactive intermediates in organic synthesis, with versatile synthetic utilities in processes such as hydrogen-atom transfer (HAT), β-fragmentation, radical addition to unsaturated carbon–carbon bonds, and rearrangement reactions. In this review, we focus on recent advances in the generation and transformation of oxygen-centered radicals, including (alkyl-, α-oxo-, aryl-) carboxyl, alkoxyl, aminoxyl, phenoxyl, and vinyloxyl radicals, and compare the reactivity of oxygen-centered radicals under traditional reaction conditions with their reactivity under visible-light-induced reaction conditions.

Ultrasound-Promoted Organic Synthesis – A Recent Update

2021 ◽  
Vol 25 ◽  
Author(s):  
Goutam Brahmachari ◽  
Nayana Nayek ◽  
Mullicka Mandal ◽  
Anindita Bhowmick ◽  
Indrajit Karmakar
Keyword(s):  
Organic Chemistry ◽  
Green Chemistry ◽  
Organic Synthesis ◽  
Ultrasound Irradiation ◽  
Present Review ◽  
Organic Transformations ◽  
Reaction Conditions ◽  
Catalytic Systems ◽  
Bond Forming ◽  
Reducing Energy

: Ultrasonication, nowadays, is well-regarded as an effective green tool in implementing a plethora of organic transformations. The last decade has seen quite useful applications of ultrasound irradiation in synthetic organic chemistry. Ultrasound has already come out as a unique technique in green chemistry practice, for its inherent properties of minimizing wastes and reducing energy and time, thereby increasing the product yields with higher purities under milder reaction conditions. The present review summarizes ultrasound-promoted useful organic transformations involving both carbon-carbon and carbon-heteroatom (N, O, S) bond-forming reactions in the absence or presence of varying catalytic systems, reported during the period 2016-2020.

Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent

2011 ◽  
Vol 65 (3) ◽  
Author(s):  
Selvaraj Roopan ◽  
Fazlur-Rahman Khan ◽  
Jong Jin
Keyword(s):  
Natural Product ◽  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Building Blocks ◽  
Natural Product Synthesis ◽  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Diethyl Azodicarboxylate ◽  
Nitrogen Heterocyclic

AbstractThe Mitsunobu reaction is a well-established fundamental reaction and has been widely applied in organic synthesis. In this paper, under Mitsunobu conditions dehydration proceeds between (2-chloroquinolin-3-yl)methanol and nitrogen heterocyclic compounds such as quinazolinone, pyrimidone, 2-oxoquinoline in dry THF in the presence of triethylamine, triphenylphosphane and diethyl azodicarboxylate to give the corresponding products. As part of our recent research, we attempted to couple two N-heterocyclic compounds under Mitsunobu reaction conditions to provide efficient building blocks for natural product synthesis.

Biocatalysis for Sustainable Organic Synthesis

2004 ◽  
Vol 57 (4) ◽  
pp. 281 ◽  
Author(s):  
Roger A. Sheldon ◽  
Fred van Rantwijk
Keyword(s):  
Organic Synthesis ◽  
Functional Group ◽  
Solvent System ◽  
Fine Chemicals ◽  
Reaction Conditions ◽  
Organic Syntheses ◽  
Recent Advances ◽  
Cascade Processes

Biocatalysis offers mild reaction conditions, an environmentally attractive catalyst–solvent system, high activities, and chemo-, regio-, and stereoselectivities, while the use of enzymes generally circumvents the need for functional group activation and avoids protection/deprotection steps required in traditional organic syntheses. This review, using β-lactam antibiotics as an example, discusses recent advances in biocatalysis research towards the goal of ‘green’ methodologies for the manufacture of (fine) chemicals and the emulation of a cell's enzymatic cascade processes.

scholarly journals Recent Advances in the Addition of Amide/Sulfonamide Bonds to Alkynes

Molecules ◽  
2019 ◽  
Vol 24 (1) ◽  
pp. 164 ◽  
Author(s):  
Fei Zhao ◽  
Pinyi Li ◽  
Xiaoyan Liu ◽  
Xiuwen Jia ◽  
Jiang Wang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Present Review ◽  
Reaction Conditions ◽  
Metal Free ◽  
Triple Bonds ◽  
Recent Advances ◽  
Direct Functionalization ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The addition of amide/sulfonamide bonds to alkynes is not only one of the most important strategies for the direct functionalization of carbon–carbon triple bonds, but also a powerful tool for the downstream transformations of amides/sulfonamides. The present review provides a comprehensive summary of amide/sulfonamide bond addition to alkynes, including direct and metal-free aminoacylation, based-promoted aminoacylation, transition-metal-catalyzed aminoacylation, organocatalytic aminoacylation and transition-metal-catalyzed aminosulfonylation of alkynes up to December 2018. The reaction conditions, regio- and stereoselectivities, and mechanisms are discussed and summarized in detail.

1989 göçü sonrası Bulgaristan göçmenlerinin yemek kültüründeki değişim

2017 ◽  
Vol 4 (2) ◽  
pp. 227-245
Author(s):  
Cahit Kahraman ◽  
İlhan Güneş ◽  
Nanae Kahraman
Keyword(s):  
Eating Habits ◽  
Supply And Demand ◽  
Food Culture ◽  
Rapid Progress ◽  
Canned Food ◽  
Product Range ◽  
The World ◽  
Before And After ◽  
Day By Day ◽  
Made In

1989 göçü öncesi, dünyada eşzamanlı olarak gittikçe gelişen ve zenginleşen mutfak kültürü, Bulgaristan Türklerini de etkilemiştir. Pazardaki çeşitlilik arttıkça, yemek alışkanlıkları da değişime uğramıştır. Büyük göçten sadece 30-40 sene evvel kısıtlı imkânlar ile sınırlı sayıda yemek çeşidi üretilirken, alım gücünün artmasıyla yemek kültüründe de hızlı gelişmeler olmuştur. Artan ürün çeşitliliği yemeklere de yansımış, farklı lezzetler mutfaklara girmiştir. Göçmen yemekleri denilince hamur işleri, börek ve pideler akla gelir. Ayrıca, göçmenlerin çok zengin turşu, komposto ve konserve kültürüne sahip oldukları da bilinir. Bu çalışma, 1989 öncesi Bulgaristan’ın farklı bölgelerinde yaşayan Türklerin yemek alışkanlıklarına ışık tutmakla birlikte, göç sonrasında göçmen mutfak kültüründe bir değişiklik oluşup oluşmadığını konu almaktadır. Bu amaçla, 1989 yılında Türkiye’ye göç etmiş 50 kişiye 8 sorudan oluşan anket düzenlenmiştir. Bu verilerden yola çıkarak oluşan bulgular derlenmiş ve yeni tespitler yapılmıştır. Ayrıca, Türkiye’nin farklı bölgelerine yerleşen göçmenler, kendi göçmen pazarlarını kurmuşlardır. Bulgaristan’dan getirilen ürünlerin bu pazarlarda satılması böyle bir arz talebin hala devam ettiğine işaret etmektedir.ABSTRACT IN ENGLISHThe Diversity in Cuisine Culture of the Immigrants from Bulgaria After 1989 MigrationThe Cuisine culture that has been developing and getting rich day by day contemporaneously in the world before 1989 migration has also had an impact on Bulgarian Turks. By the increase in diversity in the market, eating habits have changed. While producing a limited number of food types with limited opportunities just some 30 or 40 years before the ‘Big Migration’, there has been a rapid progress in food culture by the help of the increase in purchase power. Enhancing product range has been reflected in food, and different tastes have entered the cuisines. When we say immigrant, the first things that come to our mind are pastry, flan and pitta bread. Moreover, it is also known that immigrants have a very rich cuisine culture of pickle, stewed fruit, and canned food. This study aims both to disclose the eating habits of Turks living in different regions of Bulgaria before 1989 and to determine whether there has been a difference in immigrant cuisine culture before and after the migration. For this purpose, a questionnaire consisting of 8 questions has been administered to 50 people who migrated to Turkey in 1989. The results gathered from these data have been compiled and new determinations have been made. In addition, immigrants that settled in different regions of Turkey have set their own immigrant markets. The fact that the products brought from Bulgaria are being sold in these markets shows that this kind of supply and demand still continues.

Urea-Catalyzed Functionalization of Unactivated C–H Bonds

2020 ◽  
Author(s):  
Alex L. Bagdasarian ◽  
Stasik Popov ◽  
Benjamin Wigman ◽  
Wenjing Wei ◽  
woojin lee ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Organic Synthesis ◽  
High Energy ◽  
Acid Catalysts ◽  
Potential Utility ◽  
New Paradigm ◽  
Lewis Acid Catalysts ◽  
Reaction Conditions ◽  
Highly Active ◽  
Acidic Nature

Herein we report the 3,5bistrifluoromethylphenyl urea-catalyzed functionalization of unactivated C–H bonds. In this system, the urea catalyst mediates the formation of high-energy vinyl carbocations that undergo facile C–H insertion and Friedel–Crafts reactions. We introduce a new paradigm for these privileged scaffolds where the combination of hydrogen bonding motifs and strong bases affords highly active Lewis acid catalysts capable of ionizing strong C–O bonds. Despite the highly Lewis acidic nature of these catalysts that enables triflate abstraction from sp<sup>2</sup> carbons, these newly found reaction conditions allow for the formation of heterocycles and tolerate highly Lewis basic heteroaromatic substrates. This strategy showcases the potential utility of dicoordinated vinyl carbocations in organic synthesis.<br>

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