scholarly journals Cobalt Catalysis Enables Regioselective Ring-opening of Epoxides with Aryl Halides

2021 ◽  
Author(s):  
Aleksandra Potrząsaj ◽  
Mateusz Musiejuk ◽  
Wojciech Chaładaj ◽  
Maciej Giedyk ◽  
Dorota Gryko
Keyword(s):  
Vitamin B12 ◽  
Organic Synthesis ◽  
Blue Light ◽  
Catalytic System ◽  
Ring Opening ◽  
Aryl Halides ◽  
Light Irradiation ◽  
Selective Synthesis ◽  
Ring Opening Of Epoxides

Ring-opening of epoxides furnishing either linear or branched products belongs to the group of classic transformations in organic synthesis. However, the regioselective cross-electrophile coupling of aryl epoxides with aryl halides still represents a key challenge. Herein, we report vitamin B12/Ni dual-catalytic system that allows for the selective synthesis of linear products under blue-light irradiation.

scholarly journals Cobalt Catalysis Enables Regioselective Ring-opening of Epoxides with Aryl Halides

2021 ◽  
Author(s):  
Aleksandra Potrząsaj ◽  
Mateusz Musiejuk ◽  
Wojciech Chaładaj ◽  
Maciej Giedyk ◽  
Dorota Gryko
Keyword(s):  
Vitamin B12 ◽  
Organic Synthesis ◽  
Blue Light ◽  
Catalytic System ◽  
Ring Opening ◽  
Aryl Halides ◽  
Light Irradiation ◽  
Selective Synthesis ◽  
Ring Opening Of Epoxides

Ring-opening of epoxides furnishing either linear or branched products belongs to the group of classic transformations in organic synthesis. However, the regioselective cross-electrophile coupling of aryl epoxides with aryl halides still represents a key challenge. Herein, we report vitamin B12/Ni dual-catalytic system that allows for the selective synthesis of linear products under blue-light irradiation.

scholarly journals Asymmetric Ring-Opening of Epoxides Catalyzed by Metal–Salen Complexes

Catalysts ◽  
2020 ◽  
Vol 10 (6) ◽  
pp. 705
Author(s):  
Anna Lidskog ◽  
Yutang Li ◽  
Kenneth Wärnmark
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Ring Opening ◽  
Kinetic Resolution ◽  
Catalytic Systems ◽  
Salen Complexes ◽  
Epoxide Opening ◽  
Ring Opening Of Epoxides ◽  
One Step ◽  
Asymmetric Ring Opening

The asymmetric ring-opening of epoxides is an important reaction in organic synthesis, since it allows for the enantioselective installation of two vicinal functional groups with specific stereochemistry within one step from a highly available starting material. An effective class of catalysts for the asymmetric ring-opening of epoxides is metal–salen complexes. This review summarizes the development of metal–salen catalyzed enantioselective desymmetrization of meso-epoxides and kinetic resolution of epoxides with various nucleophiles, including the design and application of both homogeneous- and heterogeneous epoxide-opening catalysts as well as multi-metallic covalent and supramolecular catalytic systems.

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

Blue Light Enhanced Heck Arylation at Room Temperature Applied to Allenes

2022 ◽  
Author(s):  
Polyssena Renzi ◽  
Emanuele Azzi ◽  
Enrico Bessone ◽  
Giovanni Ghigo ◽  
Stefano Parisotto ◽  
...  
Keyword(s):  
Visible Light ◽  
Blue Light ◽  
Catalytic System ◽  
Heck Reaction ◽  
Room Temperature ◽  
Aryl Halides ◽  
Heck Arylation

An unprecedented visible light enhanced room temperature Heck reaction between aryl halides and allenyl tosyl amines is here reported. The simple catalytic system (Pd(OAc)2/PPh3) is exploited to afford arylated vinyl...

scholarly journals Visible-Light Reductive Cyclization of Nonactivated Alkyl Chlorides

Synlett ◽  
2019 ◽  
Vol 30 (13) ◽  
pp. 1496-1507
Author(s):  
Miguel Claros ◽  
Alicia Casitas ◽  
Julio Lloret-Fillol
Keyword(s):  
Visible Light ◽  
Vitamin B12 ◽  
Catalytic System ◽  
Catalyst Design ◽  
Light Irradiation ◽  
Reductive Cyclization ◽  
Visible Light Photocatalysis ◽  
Reduction Potentials ◽  
Organic Halides ◽  
Chemical Inertness

Nonactivated alkyl chlorides are readily available and bench-stable feedstocks; however, they exhibit an inherent chemical inertness, in part, due to their large negative reduction potentials, which have precluded their widespread use as radical precursors in visible-light photocatalysis. Herein, we highlight some recent strategies for activating challenging organic halides under light irradiation, with special emphasis in C(sp3)–halide bonds. In this line, a brief summary of the reactivity of Vitamin B12, F430 cofactor and derivatives is required to comprehend the chemistry behind our developed Cu/M (M = Co, Ni) dual catalytic system. Catalyst design has been key for developing a mild and general photoredox methodology for the intramolecular reductive cyclization of nonactivated alkyl chlorides with tethered alkenes. The cleavage of strong C(sp3)–Cl bonds is mediated by a highly nucleophilic low-valent cobalt or nickel intermediate generated by visible-light photoredox reduction employing a copper photosensitizer.

Diethylaluminium Azide: A Versatile Reagent in Organic Synthesis

2015 ◽  
Vol 68 (5) ◽  
pp. 703 ◽  
Author(s):  
Serena Monticelli ◽  
Vittorio Pace
Keyword(s):  
Organic Synthesis ◽  
Lewis Acid ◽  
Ring Opening ◽  
Fullerene C60 ◽  
Ring Opening Of Epoxides ◽  
Acyl Azides ◽  
Versatile Reagent

The unique properties of diethylaluminium azide – arising from the Lewis acid aluminium and the nucleophilicity of the azide – make it a versatile reagent in organic synthesis. Ring-opening of epoxides, Michael-type additions, synthesis of acyl azides, and functionalizations of fullerene C60 will be discussed. Among the recently described uses of the reagent, particular attention will be devoted to the powerful Sedelmeier’s method to access 1H-tetrazol starting from nitriles.

Selective aerobic oxidation of sulfides to sulfoxides in water under blue light irradiation over Bi4O5Br2

2020 ◽  
Vol 22 (15) ◽  
pp. 4884-4889 ◽  
Author(s):  
Wei Zhao ◽  
Chunxia Yang ◽  
Jindi Huang ◽  
Xiaoli Jin ◽  
Yu Deng ◽  
...  
Keyword(s):  
Blue Light ◽  
Catalytic System ◽  
Aerobic Oxidation ◽  
Light Irradiation ◽  
Oxidation Of Sulfides ◽  
Selective Aerobic Oxidation

A green and practical catalytic system promoted by blue light for oxidation of sulfides to sulfoxides was successfully developed.

Sign in / Sign up

Export Citation Format

Share Document