Recent advances in aminative difunctionalization of alkenes

2021 ◽  
Author(s):  
Huanfeng Jiang ◽  
Wanqing Wu ◽  
Ziying Wu ◽  
Miao Hu ◽  
Jianxiao Li
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Recent Advances

Alkenes are versatile building blocks in modern organic synthesis. In the difunctionalization reactions of alkenes, two functional groups can be simultaneously introduced into the π system. This is an efficient...

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.

scholarly journals Recent Advances in Organocatalyzed Asymmetric Synthesis of Benzopyran and Benzodihydropyran (Chromane) Nuclei

Symmetry ◽  
2019 ◽  
Vol 11 (12) ◽  
pp. 1510
Author(s):  
Renato Dalpozzo ◽  
Raffaella Mancuso
Keyword(s):  
Natural Products ◽  
Asymmetric Synthesis ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Core Structure ◽  
The Core ◽  
Recent Advances ◽  
Set Up

Benzopyran and benzodihydropyran (chromane) nuclei are the core structure of many natural products, in particular flavonoids. Many compounds possessing this structure are nutraceuticals, pharmaceutical nutrients. Therefore, benzopyran and chromane scaffolds are important building blocks in organic synthesis and many efforts have been made to set up efficient methods for their synthesis. In particular, asymmetric methods are of great importance, being natural products, and generally chiral substances. This review aims to cover literature in the range 2017–first half of 2019.

Silylboranes as Powerful Tools in Organic Synthesis: Stereo- and Regioselective Reactions with 1,n-Enynes

Synthesis ◽  
2020 ◽  
Vol 52 (21) ◽  
pp. 3129-3139 ◽  
Author(s):  
Christina Moberg
Keyword(s):  
Metal Complexes ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Subsequent Transformation ◽  
Element Addition ◽  
Regioselective Reactions ◽  
Group 10

Bismetalated alkenes, accessible by element–element addition to alkynes, are valuable building blocks in organic synthesis, providing wide opportunities for divergent synthesis. Silaboration of alkynes with a pendant olefinic group, catalyzed by group 10 metal complexes, and subsequent transformation of the silicon and boron functional groups give access to densely functionalized 1,3-dienes and 1,3,5-trienes with defined stereo- and regiochemistry, 1,2-dienes, and carbocyclic and heterocyclic products.1 Introduction2 Background3 Reactions with 1,3-Enynes4 Cyclization 1,6-Enynes5 Cyclization 1,7-Enynes6 Cyclization of 1,n-Enynes (n > 7)7 Cyclization of Dienynes and Enediynes8 Cyclization of 1,6-Diynes9 Conclusions

Electrophilic Ring Opening of Small Heterocycles

Synthesis ◽  
2017 ◽  
Vol 49 (24) ◽  
pp. 5307-5319 ◽  
Author(s):  
Chuan Wang
Keyword(s):  
Ethylene Oxide ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Ring Opening ◽  
Building Blocks ◽  
Nickel Titanium ◽  
Ring Opening Reactions ◽  
Palladium Catalyzed ◽  
Ring Opening Of Epoxides ◽  
Nucleophilic Ring Opening

Small heterocycles, such as epoxides, aziridines, and ox­etanes are among the most useful building blocks in organic synthesis. Through electrophilic ring opening of these molecules, various electrophilic functional groups can be installed, which cannot be achieved via classic nucleophilic ring-opening reactions. In this review, the developments of electrophilic ring opening of small heterocycles are surveyed and organized according to the types of metal promoters.1 Introduction2 Electrophilic Ring Opening of Small Heterocycles Using Stoichiometric Metals2.1 Lithium-Mediated Electrophilic Ring Opening of Epoxides and Oxetanes2.2 Chromium-Mediated Electrophilic Ring Opening of Vinyl Epoxides2.3 Tin-Mediated Electrophilic Ring Opening of Vinyl Epoxides2.4 Samarium-Mediated Electrophilic Ring Opening of Vinyl and Alkynyl Epoxides2.5 Titanium-Mediated Electrophilic Ring Opening of Epoxides2.6 Platinum, Palladium, and Nickel-Mediated Electrophilic Ring Opening of 1,1-Dimethyl Ethylene Oxide3 Catalytic Electrophilic Ring Opening of Small Heterocycles3.1 Titanium-Catalyzed Electrophilic Ring Opening of Epoxides3.2 Palladium-Catalyzed Electrophilic Ring Opening of Vinyl and Alkynyl Small Heterocycles3.3 Iron-Catalyzed Electrophilic Ring Opening of Oxetanes3.4 Scandium-Catalyzed Electrophilic Ring Opening of Vinyl Epoxides3.5 Iridium-Catalyzed Electrophilic Ring Opening of 2-Methyl 2-Vinyl­oxiranes3.6 Nickel-Catalyzed Electrophilic Ring Opening of Epoxides and Aziridines3.7 Nickel–Titanium-Cocatalyzed Electrophilic Ring Opening of Epoxides4 Summary

scholarly journals Ring-Opening of Cyclodextrins: An Efficient Route to Pure Maltohexa-, Hepta-, and Octaoses

Organics ◽  
2021 ◽  
Vol 2 (3) ◽  
pp. 287-305
Author(s):  
Matthieu Pélingre ◽  
Dindet Steve-Evanes Koffi Teki ◽  
Jamal El-Abid ◽  
Vincent Chagnault ◽  
José Kovensky ◽  
...  
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Ring Opening ◽  
Building Blocks ◽  
Reaction Conditions ◽  
Strong Potential ◽  
Efficient Route ◽  
Biotechnological Processes

Many preparations of maltooligosaccharides have been described in literature, essentially using enzymatic or biotechnological processes. These compounds, derived from starch, are well-known as prebiotic agents. The use of maltohexa-, hepta-, and octaoses as synthons in organic synthesis was also well documented in literature. They can indeed be obtained as single compounds by the cyclodextrins’ ring-opening. This reaction has been studied for many years, varying the protecting and functional groups and the reaction conditions, leading to functionalized oligomaltoses. These compounds are of wide interest in various fields. They have a strong potential as scaffolds for multivalence in chemobiology, as building blocks for the production of biomimetic pseudo-glycopeptides, as well as monomers for the preparation of materials. In view of the importance of these oligomaltoses, this review focuses on the different methodologies allowing access to them via chemical and enzymatic ring-opening of cyclodextrins.

scholarly journals Recent advances in copper-catalyzed C–H bond amidation

2015 ◽  
Vol 11 ◽  
pp. 2209-2222 ◽  
Author(s):  
Jie-Ping Wan ◽  
Yanfeng Jing
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Recent Progress ◽  
Bond Formation ◽  
Carbon Sources ◽  
Copper Catalysis ◽  
Recent Advances

Copper catalysis has been known as a powerful tool for its ubiquitous application in organic synthesis. One of the fundamental utilities of copper catalysis is in the C–N bond formation by using carbon sources and nitrogen functional groups such as amides. In this review, the recent progress in the amidation reactions employing copper-catalyzed C–H amidation is summarized.

scholarly journals Synthesis of Nitroolefins via the Direct Nitration of Alkenes

SynOpen ◽  
2021 ◽  
Author(s):  
Mohamed Hassan ◽  
Cedric Ndefo Nde ◽  
Georg Manolikakes
Keyword(s):  
Organic Synthesis ◽  
Building Blocks ◽  
Recent Advances

Nitroolefins are highly versatile building blocks for organic synthesis. Herein, we want to highlight some of the most recent advances in the synthesis of nitroolefins via a direct nitration of their parent alkenes.

scholarly journals Photo-induced copper-catalyzed sequential 1,n-HAT enabling the formation of cyclobutanols

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Zhusong Cao ◽  
Jianye Li ◽  
Guozhu Zhang
Keyword(s):  
Natural Products ◽  
Hydrogen Atom ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Copper Complex ◽  
Building Blocks ◽  
Hydrogen Atom Transfer ◽  
Efficient Synthesis ◽  
Bond Functionalization ◽  
Cascade Cyclization

AbstractCyclobutanols are privileged cyclic skeletons in natural products and synthetic building blocks. C(sp3)−H functionalization is a prolonged challenge in organic synthesis. The synthesis of cyclobutanols through double C(sp3)-H bond functionalization remains elusive. Here we report the efficient synthesis of cyclobutanols through intermolecular radical [3 + 1] cascade cyclization, involving the functionalization of two C − H bonds through sequential hydrogen atom transfer. The copper complex reduces the iodomethylsilyl alcohols efficiently under blue-light irradiation to initiate the tandem transformation. The mild reaction tolerates a broad range of functional groups and allows for the facile generation of elaborate polycyclic structures.

scholarly journals Construction of C-N Bond Via Visible-Light-Mediated Difunctionalization of Alkenes

2021 ◽  
Author(s):  
Bhisma K. Patel ◽  
Tipu Alam ◽  
Amitava Rakshit
Keyword(s):  
Electron Transfer ◽  
Double Bond ◽  
Visible Light ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Bond Formation ◽  
Building Blocks ◽  
Environmental Friendliness ◽  
Visible Light Driven ◽  
Interesting Area

In the last few years, the photo-redox process via single-electron transfer (SET) has received substantial attention for the synthesis of targeted organic compounds due to its environmental friendliness and sustainability. Of late visible-light-mediated difunctionalization of alkenes has gained much attention because of its step economy, which allows the consecutive installation of two functional groups across the C=C bond in a single operation. The construction of N-containing compounds has always been important in organic synthesis. Molecules containing C-N bonds are found in many building blocks and are important precursors to other functional groups. Meanwhile, C-N bond formation via the addition of the C=C double bond is gaining prominence. Therefore, considering the influence and synthetic potential of the C-N bond, here we provide a summary of the state of the art on visible-light-driven difunctionalizations of alkene. We hope that the construction of the C-N bond via visible-light-mediated difunctionalization of alkenes will be useful for medicinal and synthetic organic chemists and will inspire further reaction development in this interesting area.

gem-Diborylalkanes: recent advances in their preparation, transformation and application

2018 ◽  
Vol 16 (7) ◽  
pp. 1050-1064 ◽  
Author(s):  
Rajender Nallagonda ◽  
Kishor Padala ◽  
Ahmad Masarwa
Keyword(s):  
Organic Synthesis ◽  
Building Blocks ◽  
Recent Advances

Recently,gem-diborylalkanes have attracted much attention as versatile building blocks and fundamental intermediates in organic synthesis, because they enable multiple C–C bond construction and further transformation at C–B bonds.

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