scholarly journals Nitrosonium ion catalysis: aerobic, metal-free cross-dehydrogenative carbon–heteroatom bond formation

2018 ◽  
Vol 54 (92) ◽  
pp. 13022-13025 ◽  
Author(s):  
Luis Bering ◽  
Laura D’Ottavio ◽  
Giedre Sirvinskaite ◽  
Andrey P. Antonchick
Keyword(s):  
Bond Formation ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Metal Free ◽  
Dehydrogenative Coupling ◽  
Nitrosonium Ion

Catalytic cross-dehydrogenative coupling of heteroarenes with thiophenols and phenothiazines has been developed under mild and environmentally benign reaction conditions.

Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products

Synthesis ◽  
2020 ◽  
Vol 52 (19) ◽  
pp. 2781-2794
Author(s):  
Till Opatz ◽  
Leander Geske ◽  
Eisuke Sato
Keyword(s):  
Organic Synthesis ◽  
Large Scale ◽  
Bond Formation ◽  
Short Review ◽  
Natural Product Synthesis ◽  
Environmentally Benign ◽  
Full Potential ◽  
Future Prospects ◽  
Reaction Conditions ◽  
Chemical Oxidants

Electrochemistry provides a valuable toolbox for organic synthesis and offers an appealing, environmentally benign alternative to the use of stoichiometric quantities of chemical oxidants or reductants. Its potential to control current efficiency along with providing alternative reaction conditions in a classical sense makes electrochemistry a suitable method for large-scale industrial transformations as well as for laboratory applications in the synthesis of complex molecular architectures. Even though research in this field has intensified over the recent decades, many synthetic chemists still hesitate to add electroorganic reactions to their standard repertoire, and hence, the full potential of preparative organic electrochemistry has not yet been unleashed. This short review highlights the versatility of anodic transformations by summarizing their application in natural product synthesis.1 Introduction2 Shono-Type Oxidation3 C–N/N–N Bond Formation4 Aryl–Alkene/Aryl–Aryl Coupling5 Cycloadditions Triggered by Oxidation of Electron-Rich Arenes6 Spirocycles7 Miscellaneous Transformations8 Future Prospects

scholarly journals Photoinduced Deaminative Borylation of Unactivated Aromatic Amines Enhanced by CO2

2021 ◽  
Author(s):  
Akira Shiozuka ◽  
Kohei Sekine ◽  
Yoichiro Kuninobu
Keyword(s):  
Aromatic Amines ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Inhibitory Effect ◽  
Light Irradiation ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Metal Free ◽  
Stoichiometric Amount ◽  
Optimal Reaction

Herein, direct unactivated C-N borylation of aromatic amines by a photocatalyst was achieved under mild and metal-free conditions. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B<sub>2</sub>pin<sub>2</sub>) proceeded in the presence of a pyrene catalyst under light irradiation (λ = 365 nm) <a>to afford desired borylated products</a> and aminoborane as a byproduct. The yield of borylated product improved under a CO<sub>2</sub> atmosphere. Reactions conducted in the presence of a stoichiometric amount of aminoborane under N<sub>2</sub> or CO<sub>2</sub> indicated that CO<sub>2</sub> reduced the inhibitory effect of aminoborane. Optimal reaction conditions were applied to a variety of aromatic amines. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.

n-Bu4NI/TBHP-catalyzed C–N bond formation via cross-dehydrogenative coupling of 1H-1,2,4-triazoles (N–H) and methylarenes (Csp3–H)

RSC Advances ◽  
2016 ◽  
Vol 6 (85) ◽  
pp. 82289-82293 ◽  
Author(s):  
Habtamu Abebe ◽  
Siddaiah Vidavalur ◽  
Venkateswara Rao Battula
Keyword(s):  
Bond Formation ◽  
Metal Free ◽  
Dehydrogenative Coupling

An efficient n-Bu4NI/TBHP-catalyzed protocol for C–N bond formation via cross-dehydrogenative coupling of 1H-1,2,4-triazoles (N–H) and methylarenes (Csp3–H) has been developed under metal free conditions.

Molecular iodine-catalysed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or sulfonamides

2009 ◽  
Vol 2009 (10) ◽  
pp. 638-641 ◽  
Author(s):  
Xufeng Lin ◽  
Jun Wang ◽  
Fangxi Xu ◽  
Yanguang Wang
Keyword(s):  
Reaction Time ◽  
Efficient Method ◽  
Bond Formation ◽  
Molecular Iodine ◽  
Allylic Alcohols ◽  
Reaction Conditions ◽  
Short Reaction Time ◽  
Metal Free ◽  
Amidation Reaction ◽  
Operational Simplicity

A highly efficient method for the C–N bond formation via 2 mol% of molecular iodine-catalysed amidation reaction of benzylic and allylic alcohols with carboxamides or sulfonamides in MeCN is described, giving the corresponding substituted amides and allylic amides in moderate to excellent yields. The significan features of the procedure include mild and metal-free reaction conditions, operational simplicity, inexpensive reagents, short reaction time, and good yields.

Methanesulfonic Acid Catalyzed Friedel–Crafts Reaction of Electron-Rich Arenes with N-Arylmaleimides: A Highly Efficient Metal-Free Route To Access 3-Arylsuccinimides

Synthesis ◽  
2021 ◽  
Author(s):  
Rama Krishna Peddinti ◽  
Deepti Gairola
Keyword(s):  
Methanesulfonic Acid ◽  
Environmentally Benign ◽  
Direct Connection ◽  
Reaction Conditions ◽  
Metal Free ◽  
Bond Forming ◽  
Highly Efficient ◽  
Acid Catalyzed

AbstractFriedel–Crafts reaction is widely used for the C–C bond forming reaction to enable the direct connection of electron-rich arenes to electron-deficient olefins with high regioselectivity. Herein, a highly efficient, metal-free, and environmentally benign F–C strategy of electron-rich arenes with N-arylmaleimides has been developed for the construction of 3-arylsuccinimides in the presence of a green reagent methanesulfonic acid under mild reaction conditions. This highly facile and high-yielding protocol has compatibility with different electron-rich arenes.

Oxidative cross dehydrogenative coupling between iodoarenes and acylanilides for C–N bond formation under metal-free conditions

2021 ◽  
Author(s):  
Peng Yang ◽  
Xia Wang ◽  
Liang Wang ◽  
Jiahua He ◽  
Qian Zhang ◽  
...  
Keyword(s):  
Bond Formation ◽  
Metal Catalysts ◽  
Metal Free ◽  
Dehydrogenative Coupling ◽  
Formation Method

A novel metal-free C–N bond formation method through oxidative cross dehydrogenative coupling between iodoarenes and acylanilides was developed. The reaction was mediated by mCPBA without any metal catalysts or additives....

scholarly journals Photoinduced Deaminative Borylation of Unactivated Aromatic Amines Enhanced by CO2

2021 ◽  
Author(s):  
Akira Shiozuka ◽  
Kohei Sekine ◽  
Yoichiro Kuninobu
Keyword(s):  
Aromatic Amines ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Inhibitory Effect ◽  
Light Irradiation ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Metal Free ◽  
Stoichiometric Amount ◽  
Optimal Reaction

Herein, direct unactivated C-N borylation of aromatic amines by a photocatalyst was achieved under mild and metal-free conditions. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B<sub>2</sub>pin<sub>2</sub>) proceeded in the presence of a pyrene catalyst under light irradiation (λ = 365 nm) <a>to afford desired borylated products</a> and aminoborane as a byproduct. The yield of borylated product improved under a CO<sub>2</sub> atmosphere. Reactions conducted in the presence of a stoichiometric amount of aminoborane under N<sub>2</sub> or CO<sub>2</sub> indicated that CO<sub>2</sub> reduced the inhibitory effect of aminoborane. Optimal reaction conditions were applied to a variety of aromatic amines. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.

scholarly journals N-Iodosuccinimide as a Precatalyst for Direct Cross-Coupling of Alcohols with C-Nucleophiles under Solvent-Free Reaction Conditions

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 850
Author(s):  
Njomza Ajvazi ◽  
Stojan Stavber
Keyword(s):  
Large Scale ◽  
Bond Formation ◽  
Cross Coupling ◽  
Solvent Free ◽  
Reaction Conditions ◽  
Benzyl Alcohols ◽  
Metal Free ◽  
Direct Cross ◽  
Synthetic Routes ◽  
Solvent Free Reaction

C–C bond formation is one of the most important implements in synthetic organic chemistry. In pursuit of effective synthetic routes functioning under greener pathways to achieve direct C–C bond formation, we report N-iodosuccinimide (NIS) as the most effective precatalyst among the N-halosuccinimides (NXSs) for the direct cross-coupling of benzyl alcohols with C-nucleophiles under solvent-free reaction conditions (SFRC). The protocol is metal-free, and air- and water-tolerant, providing a large-scale synthesis with almost quantitative yields.

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