Cp*Ir(iii)-catalyzed C–H/N–H functionalization of sulfoximines for the synthesis of 1,2-benzothiazines at room temperature

2018 ◽  
Vol 54 (49) ◽  
pp. 6288-6291 ◽  
Author(s):  
Yogesh N. Aher ◽  
Dhanaji M. Lade ◽  
Amit B. Pawar
Keyword(s):  
Room Temperature ◽  
Bond Functionalization ◽  
Neutral Conditions

The first Cp*Ir(iii)-catalyzed C–H/N–H bond functionalization of sulfoximines with α-diazocarbonyl compounds has been developed for the synthesis of 1,2-benzothiazines under redox-neutral conditions at room temperature.

Rh(III)-Catalyzed Olefination and Alkylation of Arenes with Maleimides: A Tunable Strategy for C(sp2)–H Functionalization

Synthesis ◽  
2021 ◽  
Author(s):  
Hongji Li ◽  
Wenjie Zhang ◽  
Xueyan Liu ◽  
Zhenfeng Tian
Keyword(s):  
Room Temperature ◽  
Functional Group ◽  
Reaction Conditions ◽  
Bond Functionalization ◽  
Alkylation Process ◽  
Coupling Partner

AbstractWe herein report a new nitrogen-directed Rh(III)-catalyzed C(sp2)–H bond functionalization of N-nitrosoanilines and azoxybenzenes with maleimides as a coupling partner, in which the olefination/alkylation process can be finely controlled at room temperature by variation of the reaction conditions. This method shows excellent functional group tolerance, and presents a mild access to the resulting olefination/alkylation products in moderate to good yields.

Organophotoredox-Catalyzed C–H Alkylation of Imidazoheterocycles with Malonates: Total Synthesis of Zolpidem

Synthesis ◽  
2020 ◽  
Author(s):  
Narendra R. Chaubey ◽  
Anant R. Kapdi ◽  
Biswanath Maity
Keyword(s):  
Total Synthesis ◽  
Room Temperature ◽  
Drug Molecule ◽  
Bond Functionalization ◽  
First Report ◽  
Mild Conditions ◽  
The Past ◽  
Hypnotic Drug ◽  
Free Environment

AbstractOrganophotocatalytic C–H bond functionalization has attracted a lot of attention in the past several years due to the possibility of catalyzing reactions in a metal- and peroxide-free environment. Continuing on these lines, an organophotoredox-catalyzed C–H functionalization of imidazo[1,2-a]pyridines and related heterocycles with bromomalonates under mild conditions is reported, providing excellent yields of the products at room temperature. This is the first report involving malonates as coupling partners leading to the synthesis of a range of functionalized products including total synthesis of zolpidem, a sedative­-hypnotic drug molecule.

scholarly journals A Facile Synthesis of Polysubstituted Pyrroles by One-Pot Three-Component Reaction

2012 ◽  
Vol 9 (4) ◽  
pp. 2239-2244 ◽  
Author(s):  
Hossein Anaraki-Ardakani ◽  
Maziar Noei ◽  
Mina Karbalaei-Harofteh ◽  
Shahab Zomorodbakhsh
Keyword(s):  
Room Temperature ◽  
Facile Synthesis ◽  
One Pot ◽  
Pyrrole Derivatives ◽  
Dialkyl Acetylenedicarboxylates ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields ◽  
Neutral Conditions

A new and efficient one-pot synthesis of polysubstituted pyrrole derivatives by three-component reaction between dialkyl acetylenedicarboxylates, triphenylphosphine, 2-aminopyridin derivatives in the presence of arylglyoxals is described. The reactions were performed in dichloromethane at room temperature and neutral conditions and afforded high yields of products.

Solid lithium perchlorate as a powerful catalyst for the synthesis of β-aminoalcohols under solvent-free conditions

2005 ◽  
Vol 83 (5) ◽  
pp. 505-507 ◽  
Author(s):  
Najmodin Azizi ◽  
Mohammad R Saidi
Keyword(s):  
Ring Opening ◽  
Room Temperature ◽  
Lithium Perchlorate ◽  
Solvent Free ◽  
Solvent Free Conditions ◽  
Reaction Proceeds ◽  
Ring Opening Of Epoxides ◽  
Neutral Conditions ◽  
Hindered Amines ◽  
Short Times

Lithium perchlorate catalyzed the ring opening of epoxides with amines to provide the corresponding β-aminoalcohols in excellent yields with high regioselectivity. The reaction proceeds rapidly under mild and neutral conditions and worked well with primary, secondary, aliphatic, aromatic, and hindered amines in short times at room temperature, in the absence of solvent.Key words: epoxide, lithium perchlorate, β-aminoalcohols, solvent-free.

scholarly journals Site-selective remote C(sp3)–H heteroarylation of amides via organic photoredox catalysis

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Hui Chen ◽  
Wenjing Fan ◽  
Xiang-Ai Yuan ◽  
Shouyun Yu
Keyword(s):  
Hydrogen Atom ◽  
Room Temperature ◽  
Ph Value ◽  
Metal Free ◽  
Selective Functionalization ◽  
Site Selectivity ◽  
Hydrogen Atom Transfers ◽  
Site Selective ◽  
Neutral Conditions ◽  
Potential Complement

Abstract Radical translocation processes triggered by nitrogen-centered radicals (NCRs), such as 1,5-hydrogen atom transfers (1,5-HAT), demonstrated by the well-established Hofmann-Löffler-Freytag (HLF) reaction, provide an attractive approach for the controllable and selective functionalization of remote inert C(sp3)–H bonds. Here we report an amidyl radical-triggered site-selective remote C(sp3)–H heteroarylation of amides under organic photoredox conditions. This approach provides a mild and highly regioselective reaction affording remote C(sp3)–H heteroarylated amides at room temperature under transition-metal free, weakly basic, and redox-neutral conditions. Non-prefunctionalized heteroarenes, such as purines, thiazolopyridines, benzoxazole, benzothiazoles, benzothiophene, benzofuran, thiazoles and quinoxalines, can be alkylated directly. Sequential and orthogonal C–H functionalization of different heteroarenes by taking advantage pH value or polarity of radicals has also been achieved. DFT calculations explain and can predict the site-selectivity and reactivity of this reaction. This strategy expands the scope of the Minisci reaction and serves as its alternative and potential complement.

scholarly journals Efficient one-pot, four-component synthesis of N,N-dibenzyl-N-{1-[5-(3-aryl)-1,3,4-oxadiazol-2-yl]cyclobutyl}amine derivatives from the reaction of (isocyanoimino)triphenylphosphorane, dibenzylamine, an aromatic carboxylic acid and cyclobutanone

2012 ◽  
Vol 77 (9) ◽  
pp. 1175-1180 ◽  
Author(s):  
Nahid Shajari ◽  
Reza Kazemizadeh ◽  
Ali Ramazani
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Aromatic Carboxylic Acid ◽  
One Pot ◽  
Aromatic Carboxylic Acids ◽  
High Yields ◽  
Neutral Conditions

Four-component reaction of cyclobutanone, dibenzylamine and (Nisocyanimino) triphenylphosphorane in the presence of aromatic carboxylic acids proceed smoothly at room temperature and under neutral conditions to afford N,N-dibenzyl-N-{1-[5-(3-aryl)-1,3,4-oxadiazol-2-yl]cyclobutyl}amine derivatives in high yields.

Investigation of Phthalocyanine Catalysts for the Aerobic Synthesis of meso-Substituted Porphyrins

1997 ◽  
Vol 01 (04) ◽  
pp. 385-394 ◽  
Author(s):  
M. RAVIKANTH ◽  
CATALINA ACHIM ◽  
JOHN S. TYHONAS ◽  
ECKARD MÜNCK ◽  
JONATHAN S. LINDSEY
Keyword(s):  
Trifluoroacetic Acid ◽  
Room Temperature ◽  
Heterogeneous Catalysts ◽  
Mossbauer Spectroscopy ◽  
Oxidation Process ◽  
Aerobic Oxidation ◽  
Heterogeneous Reactions ◽  
High Concentration ◽  
Neutral Conditions ◽  
Homogeneous Reactions

The aerobic oxidation process for the synthesis of porphyrins, previously performed using 5 mol % p-chloranil (TCQ), 5 mol % iron(II) phthalocyanine ( FePc ) and stoichiometric amounts of O 2, has been refined using new phthalocyanine catalysts. Four phthalocyanine catalysts have been prepared, characterized by Mössbauer spectroscopy and examined for efficacy in the high concentration (0.1 M) synthesis of tetraphenylporphyrin at room temperature. Each phthalocyanine has been identified to be a μ-oxo dimer. Two catalysts are soluble (the μ-oxo dimers [(t-butyl)4 FePc ]2 O and [(n- C 6 H 13 O )4 FePc ]2 O ) and enable homogeneous reactions, while two are insoluble (the μ-oxo(1) and μ-oxo(2) dimers of FePc , ( FePc )2 O ) and give heterogeneous reactions. These four phthalocyanine compounds provide efficient catalysis at the 0.3–1 mol % level using only 1 mol % quinone or hydroquinone ( TCQ , DDQ , TCQH 2 or DDQH 2), affording ~25% yields of tetraphenylporphyrin in 60 min of oxidation. There are no discernible advantages of the homogeneous versus heterogeneous catalysts. The μ-oxo dimers are active, but FePc is inactive, at the 0.3 mol % level. The activity of the FePc sample at the 5 mol % level is attributed to residual μ-oxo dimer impurity. This aerobic oxidation process is superior to stoichiometric oxidation with TCQ or DDQ , and can be performed in the presence of BF 3· O ( Et )2, trifluoroacetic acid, or under neutral conditions.

scholarly journals Organophotoredox-Catalyzed Direct C-H Functionalization of “Drug Prejudice” at Room Temperature

2020 ◽  
Author(s):  
Narendra Chaubey ◽  
Anant Kapdi ◽  
Biswanath Maity
Keyword(s):  
Room Temperature ◽  
Bond Functionalization ◽  
First Report ◽  
Metal Free ◽  
Mild Conditions ◽  
The Past ◽  
Free Environment

<p>Organophotocatalytic C─H bond functionalization has attracted lot of attention in the past several years due to the possibility of catalysing reactions in a metal-free environment. Continuing on these lines, we repot herein an organophotoredox catalyzed C─H functionalization of imidazo[1,2-a]pyridines and related heterocycles with malonates under mild conditions providing excellent yields of the products at room temperature. Although, C─3 functionalization of imidazo[1,2-a]pyridines are known, this is the first report involving malonates as coupling partners leading to the synthesis of a range of functionalized products including Zolpidem, a sedative-hypnotic medicine. </p>

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