Novel Addition and [3+2] Cycloaddition Reactions of Stannyl- and Silyl-ortho-carboranes to Carbonyl Compounds

1999 ◽  
Vol 64 (5) ◽  
pp. 829-846 ◽  
Author(s):  
Hiroyuki Nakamura ◽  
Yoshinori Yamamoto
Keyword(s):  
Carbonyl Compounds ◽  
Addition Reaction ◽  
Cycloaddition Reactions ◽  
Tetrabutylammonium Fluoride ◽  
High Yields

Stannyl- and silyl-ortho-carboranes serve as an ortho-carborane carbanion equivalents in the addition reaction to aldehydes. The reaction of (tributylstannyl)-ortho-carborane 2 with aldehydes 4 in the presence of palladium(0) catalysts gave the corresponding (ortho-carboranyl) carbinols 5 in good to high yields. The reaction of (trimethylsilyl)-ortho-carborane 3 with aldehydes 4 in the presence of tetrabutylammonium fluoride (TBAF) gave the corresponding (ortho-carboranyl) carbinols 5 in high yields. Furthermore, (trimethylsilyl)-ortho-carborane 3 underwent a facile [3+2] annulation reaction with various α,β-unsaturated enals and enones in the presence of tetrabutylammonium fluoride, giving the corresponding five-membered carboracyclic products 14 in good to high yields.

scholarly journals Synthesis and Antiproliferative Evaluation of 2-Deoxy-N-glycosylbenzotriazoles/imidazoles

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3742
Author(s):  
Caleigh S. Garton ◽  
Noelle K. DeRose ◽  
Dylan Dominguez ◽  
Maria L. Turbi-Henderson ◽  
Ashley L. Lehr ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Addition Reaction ◽  
Protecting Group ◽  
Human Breast ◽  
Lung Cancer Cell ◽  
Subsequent Removal ◽  
Anticancer Properties ◽  
Tributyltin Hydride ◽  
High Yields

A series of 2-deoxy-2-iodo-α-d-mannopyranosylbenzotriazoles was synthesized using the benzyl, 4,6-benzylidene and acetyl protected D-glucal in the presence of N-iodosuccinimide (NIS). Subsequent removal of the iodine at the C-2 position using tributyltin hydride under free radical conditions afforded the 2-deoxy-α-d-glucopyranosylbenzotriazoles in moderate to high yields. This method was extended to the preparation of substituted 2-deoxy-β-d-glucopyranosylimidazoles as well. The stereoselectivity of the addition reaction and the effect of the protecting group and temperature on anomer distribution of the benzotriazole series were also investigated. The anticancer properties of the newly synthesized compounds were evaluated in a series of viability studies using HeLa (human cervical adenocarcinoma), human breast and lung cancer cell lines. The N-[3,4,6-tri-O-benzyl-2-deoxy-α-d-glucopyranosyl]-1H-benzotriazole and the N-[3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl]-2H-benzotriazole were found to be the most potent cancer cell inhibitors at 20 µM concentrations across all four cell lines.

scholarly journals Copper(I) Chloride/Kieselguhr: A Versatile Catalyst for Oxidation of Alkyl Halides and Alkyl Tosylates to the Carbonyl Compounds

1999 ◽  
Vol 23 (7) ◽  
pp. 434-435
Author(s):  
Mohammed M. Hashemi ◽  
Yousef Ahmadi Beni
Keyword(s):  
Carbonyl Compounds ◽  
Alkyl Halides ◽  
Aldehydes And Ketones ◽  
High Yields

Copper(I) Chloride adsorbed on Kieselguhr in the presence of oxygen catalyses oxidation of alkyl halides and alkyl tosylates to the aldehydes and ketones in high yields.

Studies on electrooxidation of lignin and lignin model compounds. Part 1: Direct electrooxidation of non-phenolic lignin model compounds

Holzforschung ◽  
2012 ◽  
Vol 66 (3) ◽  
Author(s):  
Takumi Shiraishi ◽  
Toshiyuki Takano ◽  
Hiroshi Kamitakahara ◽  
Fumiaki Nakatsubo
Keyword(s):  
Electron Transfer ◽  
Cyclic Voltammetry ◽  
Carbonyl Compounds ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Bulk Electrolysis ◽  
Lignin Model ◽  
Dimeric Compound ◽  
High Yields ◽  
Short Time

Abstract The direct anodic oxidation of non-phenolic lignin model compounds was investigated to understand their basic behaviors. The results of cyclic voltammetry (CV) studies of monomeric model, such as 1-(4-ethoxy-3-methoxyphenyl)ethanol, are interpreted as the oxidation for Cα-carbonylation did not proceed in the reaction without a catalyst, but a base promotes this reaction. Indeed, the bulk electrolyses of the monomeric lignin model compounds with 2,6-lutidine afforded the corresponding Cα-carbonyl compounds in high yields (60–80%). It is suggested that deprotonation at Cα-H in the ECEC mechanism (E=electron transfer and C=chemical step) is important for Cα-carbonylation. In the uncatalyzed bulk electrolysis of a β-O-4 model dimeric compound, 4-ethoxy-3-methoxyphenylglycerol-β-guaiacyl ether, the corresponding Cα-carbonyl compound was not detected but as a result of Cα-Cβcleavage 4-O-ethylvanillin was found in 40% yield. In the electrolysis reaction in the presence of 2,6-lutidine (as a sterically hindered light base), the reaction stopped for a short time unexpectedly. These results indicate the different electrochemical behavior of simple monomeric model compounds and dimeric β-O-4 models. The conclusion is that direct electrooxidation is unsuitable for Cα-carbonylation of lignin.

Hypervalent iodine catalysis for selective oxidation of Baylis–Hillman adducts via in situ generation of o-iodoxybenzoic acid (IBX) from 2-iodosobenzoic acid (IBA) in the presence of oxone

2016 ◽  
Vol 40 (12) ◽  
pp. 10300-10304 ◽  
Author(s):  
Raktani Bikshapathi ◽  
Parvathaneni Sai Prathima ◽  
Vaidya Jayathirtha Rao
Keyword(s):  
Selective Oxidation ◽  
Carbonyl Compounds ◽  
Hypervalent Iodine ◽  
In Situ Generation ◽  
Iodosobenzoic Acid ◽  
High Yields

An efficient, eco-friendly protocol for selective oxidation of primary and secondary Baylis–Hillman alcohols to the corresponding carbonyl compounds in high yields has been developed with 2-iodosobenzoic acid (IBA).

Novel Ceric Ammonium Nitrate-Stabilized Maghemite Nanoparticles (CAN-γ-Fe2O3) for Ultrasound Assisted Synthesis of β-Amino Derivatives

2021 ◽  
Author(s):  
Anurag Kumar ◽  
Yifat Harel ◽  
Jean-paul Lellouche ◽  
Suman L. Jain
Keyword(s):  
Carbonyl Compounds ◽  
Addition Reaction ◽  
Ceric Ammonium Nitrate ◽  
Reusable Catalyst ◽  
Maghemite Nanoparticles ◽  
Reaction Conditions ◽  
Recyclable Catalysts ◽  
Nucleophilic Addition Reaction ◽  
Amino Derivatives ◽  
Positively Charged

Abstract Owing to their inherent features like smaller size and higher surface area exposed to reactants, nanoparticles have gained enormous interest and are extensively used as magnetically recyclable catalysts for various organic reactions. Herein, we report highly hydrophilic, non-aggregated, and strongly positively charged (ζ potential: +45.7 mV) ultra-small cerium cations/complexes- stabilized maghemite nanoparticles in water as an efficient and reusable nanoscaled magnetically active catalyst for the nucleophilic addition reaction of various amines with α,β-unsaturated carbonyl compounds to give corresponding β-amino derivatives under ultrasonic irradiation. The developed protocol provides several merits such as high product yields, mild reaction conditions, reusable catalyst and easy workup.

Tandem dihetero-Diels–Alder and Huisgen cycloaddition reactions. Synthesis, crystal structure and hydrolysis of the novel cage phosphoranes

2018 ◽  
Vol 5 (21) ◽  
pp. 3113-3128 ◽  
Author(s):  
Nadezhda R. Khasiyatullina ◽  
Tamara A. Baronova ◽  
Ekaterina V. Mironova ◽  
Robert R. Fayzullin ◽  
Igor A. Litvinov ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Carbonyl Compounds ◽  
Diels Alder ◽  
Cycloaddition Reactions ◽  
The Novel ◽  
Hydrolysis Of

The reaction of 2-(1-phenylvinyloxy)benzo-1,3,2-dioxaphosphole with activated carbonyl compounds leads to the stereoselective formation of cage phosphoranes.

Tin(II)chloride Mediated Addition Reaction of Bromonitromethane to Aldehydes

2005 ◽  
Vol 60 (4) ◽  
pp. 416-418 ◽  
Author(s):  
Ali S. Mahasneh
Keyword(s):  
Mass Spectroscopy ◽  
Elemental Analysis ◽  
Addition Reaction ◽  
Aromatic Aldehydes ◽  
Aliphatic Aldehydes ◽  
Type Reaction ◽  
High Yields

Bromonitromethane adds to aliphatic aldehydes in the presence of tin(II) chloride to yield β -nitro alcohols via a Reformatsky-type reaction in high yields, while aromatic aldehydes give low yields. The products were characterized by IR, NMR, and mass spectroscopy and by elemental analysis

Cyclopropenium-Activated DMSO for Swern-Type Oxidation

Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 329-332 ◽  
Author(s):  
Tianfo Guo ◽  
Yu Gao ◽  
Zhenjiang Li ◽  
Jingjing Liu ◽  
Kai Guo
Keyword(s):  
Conventional Method ◽  
Carbonyl Compounds ◽  
Oxalyl Chloride ◽  
Fast Reactions ◽  
Broad Scope ◽  
New Type ◽  
High Yields ◽  
Swern Oxidation ◽  
Easy Operation

Swern oxidation is widely used to convert alcohols into their corresponding carbonyl compounds. However, the conventional method with use of the volatile oxalyl chloride as an activator requires the reaction to be conducted below −60 °C. We discovered that 3,3-dichloro-1,2-diphenylcyclopropene (DDC) can be used as a new activator for Swern-type oxidations of alcohols, which can be conducted at −20 °C. This new protocol features mild and fast reactions with easy operation. Furthermore, the activator DDC is easy to handle, and diphenylcyclopropenone can be recovered quantitively. This new type of Swern oxidation shows a broad scope of substrates including benzylic, allylic, aliphatic, and biobased alcohols, and gives high yields of up to 93%.

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