Direct functionalization of cyclic ethers with maleimide iodides via free radial-mediated sp3 C–H activation

2021 ◽  
Author(s):  
Xiaoyu Cheng ◽  
Baojun Li ◽  
Mengsi Zhang ◽  
Haotian Lu ◽  
Wenbo Wang ◽  
...  
Keyword(s):  
Free Radical ◽  
Bond Formation ◽  
Cyclic Ethers ◽  
Reaction Conditions ◽  
Formation Reaction ◽  
Direct Functionalization

A new C–C bond formation reaction was developed through free radical-initiated direct C–H activation of cyclic ethers with maleimide iodides under mild reaction conditions.

Metal-free, radical 1,6-conjugated addition of cyclic ethers with para-quinone methides (p-QMs)

2019 ◽  
Vol 17 (12) ◽  
pp. 3239-3248 ◽  
Author(s):  
Satish G. More ◽  
Gurunath Suryavanshi
Keyword(s):  
Free Radical ◽  
Efficient Method ◽  
Bond Formation ◽  
Cyclic Ethers ◽  
Quinone Methides ◽  
Metal Free

An efficient method for metal-free C–C bond formation between p-quinone methides (p-QMs) and cyclic ethers via a radical pathway to afford substituted diarylmethanes and triarylmethanes or to effect the α-alkylation of the cyclic ethers has been developed.

scholarly journals Palladium-Catalyzed Approach to Allenic Aromatic Ethers and First Total Syntheses of Terricollene A

2021 ◽  
Author(s):  
Chaofan Huang ◽  
Fuchun Shi ◽  
Yifan Cui ◽  
Can Li ◽  
Jie Lin ◽  
...  
Keyword(s):  
Bond Formation ◽  
Reaction Conditions ◽  
Formation Reaction ◽  
Total Syntheses ◽  
Palladium Catalyzed

A palladium-catalyzed C-O bond formation reaction between phenols and allenylic carbonates to give 2,3-allenic aromatic ethers with decent to excellent yields under mild reaction conditions has been described. A variety...

Ru-catalyzed oxidation and C–C bond formation of indoles for the synthesis of 2-indolyl indolin-3-ones under mild reaction conditions

2020 ◽  
Vol 98 (11) ◽  
pp. 667-669
Author(s):  
Xiao-Yu Zhou ◽  
Xia Chen
Keyword(s):  
Catalytic Oxidation ◽  
Bond Formation ◽  
High Yield ◽  
Target Product ◽  
Reaction Conditions ◽  
Formation Reaction ◽  
Butyl Hydroperoxide ◽  
Tert Butyl Hydroperoxide ◽  
Catalyzed Oxidation ◽  
Oxidation System

Herein, we described a ruthenium catalyzed oxidation and C–C bond formation reaction of 2-alkyl or 2-aryl substituted indoles using tert-butyl hydroperoxide (TBHP) as oxidant. Coupled with cascade transformation, it provided a mild catalytic oxidation system for the synthesis of 2-indolylindolin-3-ones. The reaction could readily occur using RuCl3·3H2O as catalyst, and the target product was obtained with medium to high yield.

scholarly journals Pd-catalyzed C(sp3)–C(sp) bond formation in iodocyclobutenes

2021 ◽  
Author(s):  
Pedro Almendros ◽  
Carlos Lázaro-Milla ◽  
M. Teresa Quiros ◽  
Diego J Cardenas
Keyword(s):  
Bond Formation ◽  
Formation Reaction ◽  
Direct Functionalization

A Pd-catalyzed C(sp3)–C(sp) bond formation reaction for the synthesis of skipped 1,4-enynes through direct functionalization of the cyclobutene core with alkyne moieties has been achieved. The study of the mechanism...

Environment Friendly and Recyclable CuCl2-mediated C-S Bond Coupling Strategy Using DMEDA as Ligand, Base and Solvent

Synthesis ◽  
2021 ◽  
Author(s):  
Guodong Shen ◽  
Qichao Lu ◽  
Zeyou Wang ◽  
Weiwei Sun ◽  
Yalin Zhang ◽  
...  
Keyword(s):  
Catalytic System ◽  
Bond Formation ◽  
Environmentally Friendly ◽  
Industrial Applications ◽  
Reaction Conditions ◽  
Environment Friendly ◽  
Economic Strategy ◽  
Formation Reaction ◽  
Simple Reaction ◽  
Coupling Strategy

Simple reaction conditions and recyclable reagents are an irreplaceable advantage for environmentally friendly industrial applications. An environment friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl2 catalyzed C-S bond formation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N’-dimethylethane-1,2-diamine (DMEDA) as ligand, base and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates is compatible to give the corresponding products in good to excellent yields. Both the reaction reagents of the catalytic system (CuCl2/DMEDA) are inexpensive, conveniently separable and recyclable for more than 5 cycles.

Pd Catalyzed N1/N4 Arylation of Piperazine for Synthesis of Drugs, Biological and Pharmaceutical Targets: An Overview of Buchwald Hartwig Amination Reaction of Piperazine in Drug Synthesis

2018 ◽  
Vol 15 (2) ◽  
pp. 208-220 ◽  
Author(s):  
Vaibhav Mishra ◽  
Tejpal Singh Chundawat
Keyword(s):  
Bond Formation ◽  
Catalyst Design ◽  
Biologically Active ◽  
Reaction Conditions ◽  
Biological Targets ◽  
Amination Reaction ◽  
Drug Synthesis ◽  
Substituted Piperazine ◽  
Approved Drugs ◽  
Fda Approved Drugs

Background: Substituted piperazine heterocycles are among the most significant structural components of pharmaceuticals. N1/N4 substituted piperazine containing drugs and biological targets are ranked 3rd in the top most frequent nitrogen heterocycles in U.S. FDA approved drugs. The high demand of N1/N4 substituted piperazine containing biologically active compounds and U.S. FDA approved drugs, has prompted the development of Pd catalyzed C-N bond formation reactions for their synthesis. Buchwald-Hartwig reaction is the key tool for the synthesis of these compounds. Objective: This review provides strategies for Pd catalyzed C-N bond formation at N1/N4 of piperazine in the synthesis of drugs and biological targets with diverse use of catalyst-ligand system and reaction parameters. Conclusion: It is clear from the review that a vast amount of work has been done in the synthesis of N1/N4 substituted piperazine containing targets under the Pd catalyzed Buchwald-Hartwig amination of aryl halides by using different catalyst-ligand systems. These methods have become increasingly versatile as a result of innovation in catalyst design and improvements in reaction conditions. This review gives an overview of recent utilization of Buchwald-Hartwig amination reaction in drug/target synthesis.

Modern Organic Synthesis in the Laboratory

2008 ◽  
Author(s):  
Jie Jack Li ◽  
Chris Limberakis ◽  
Derek A. Pflum
Keyword(s):  
Organic Chemistry ◽  
Graduate Students ◽  
Organic Synthesis ◽  
Functional Group ◽  
Bond Formation ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Oxidation Reduction ◽  
Carbon Carbon Bond ◽  
Daunting Task

Searching for reaction in organic synthesis has been made much easier in the current age of computer databases. However, the dilemma now is which procedure one selects among the ocean of choices. Especially for novices in the laboratory, it becomes a daunting task to decide what reaction conditions to experiment with first in order to have the best chance of success. This collection intends to serve as an "older and wiser lab-mate" one could have by compiling many of the most commonly used experimental procedures in organic synthesis. With chapters that cover such topics as functional group manipulations, oxidation, reduction, and carbon-carbon bond formation, Modern Organic Synthesis in the Laboratory will be useful for both graduate students and professors in organic chemistry and medicinal chemists in the pharmaceutical and agrochemical industries.

scholarly journals Self-Assembled Bimetallic Aluminum-Salen Catalyst for the Cyclic Carbonates Synthesis

Molecules ◽  
2021 ◽  
Vol 26 (13) ◽  
pp. 4097
Author(s):  
Wooyong Seong ◽  
Hyungwoo Hahm ◽  
Seyong Kim ◽  
Jongwoo Park ◽  
Khalil A. Abboud ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Self Assembly ◽  
Reaction Pathway ◽  
Kinetic Studies ◽  
Cyclic Carbonate ◽  
Reaction Conditions ◽  
Formation Reaction ◽  
X Ray ◽  
Carbonate Formation ◽  
Salen Aluminum

Bimetallic bis-urea functionalized salen-aluminum catalysts have been developed for cyclic carbonate synthesis from epoxides and CO2. The urea moiety provides a bimetallic scaffold through hydrogen bonding, which expedites the cyclic carbonate formation reaction under mild reaction conditions. The turnover frequency (TOF) of the bis-urea salen Al catalyst is three times higher than that of a μ-oxo-bridged catalyst, and 13 times higher than that of a monomeric salen aluminum catalyst. The bimetallic reaction pathway is suggested based on urea additive studies and kinetic studies. Additionally, the X-ray crystal structure of a bis-urea salen Ni complex supports the self-assembly of the bis-urea salen metal complex through hydrogen bonding.

scholarly journals Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to β-Indolyl Enones and β-Pyrrolyl Enones

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1615
Author(s):  
Amy Boylan ◽  
Thien S. Nguyen ◽  
Brian J. Lundy ◽  
Jian-Yuan Li ◽  
Ravikrishna Vallakati ◽  
...  
Keyword(s):  
Positive Charge ◽  
Bond Formation ◽  
Conjugate Addition ◽  
Reaction Rates ◽  
Boronic Acids ◽  
Key Factors ◽  
Resonance Contribution ◽  
Reaction Conditions ◽  
Resonance Effects ◽  
Resonance Stabilization

Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates.

Sunlight-induced C C bond formation reaction: Radical addition of alcohols/ethers/acetals to olefins

2021 ◽  
Vol 413 ◽  
pp. 113263
Author(s):  
Mamiko Hayakawa ◽  
Hisashi Shirota ◽  
Souta Hirayama ◽  
Ryuusei Yamada ◽  
Tadashi Aoyama ◽  
...  
Keyword(s):  
Bond Formation ◽  
Radical Addition ◽  
Formation Reaction
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