126002-57-1

Upstream product

• 5535-48-8 PVS 
• 80859-83-2 1-benzene 
• 152954-27-3 -1-naphthalene 
• 152954-31-9 C₃₀H₃₅IO₈ 
• 768-94-5 1-Adamantanamine 
• 118334-83-1 1,3-dioxoisoindolin-2-yl (3r,5r,7r)-adamantane-1- carboxylate 
• 79057-62-8 O-(adamantan-1-yl) S-methyl carbonodithioate 
• 281-23-2 adamantane 
• 828-51-3 1-Adamantanecarboxylic acid 
• 35389-22-1 2-oxo-2-(adamantan-1-yloxy)acetic acid 
• 768-95-6 1-adamanthanol 
• 768-93-4 1-iodoadamantane 
• 768-90-1 1-Adamantyl bromide 
• 161564-36-9 1--4-nitrobenzene 

Relevant academic research and scientific papers

1-Ethylpiperidinium Hypophosphite: A Practical Mediator for Radical Carbon-Carbon Bond Formation

1-Ethylpiperidinium hypophosphite could be used efficiently as radical chain carrier in the intermolecular carbon-carbon bond formation without using excess of alkenes under mild reaction conditions.

Microwave-assisted tertiary carbon radical reaction for construction of quaternary carbon center

Microwave-assisted tertiary carbon radical reaction was developed. The reaction of tertiary xanthates with electron deficient alkenes was prompted by microwave irradiation, and various coupling products possessing quaternary carbon centers were obtained in good yields. The reaction was conducted under simple and common radical condition except for microwave irradiation, and the reaction completed within 5 min.

Decarboxylative Giese-Type Reaction of Carboxylic Acids Promoted by Visible Light: A Sustainable and Photoredox-Neutral Protocol

We describe herein a transition-metal-free method for the decarboxylative generation of radicals from carboxylic acids and their 1,4-addition to Michael acceptors. The Fukuzumi catalyst (9-mesitylene-10-methylacridinium perchlorate, [Acr-Mes]ClO4) enabled this transformation under visible-light irradiation at room temperature with CO2 as the only byproduct. The scope and limitations of this protocol were examined by using a range of Michael acceptors (15 examples) and carboxylic acids (18 examples). The use of 3-hydroxypivalic acid in this protocol allowed the straightforward formation of a diastereomerically pure δ-lactone. Moreover, when a homoallylic acid was used, a radical cascade reaction took place with the formation of three C–C bonds.

Photoredox-catalyzed deaminative alkylation via C-N bond activation of primary amines

Primary amines are often cheap, naturally occurring, and chemically diverse starting materials. For these reasons, deaminative functionalization of amines has emerged as an important area of research. Recent advances in C-N activation transform simple α-1° and α-2° amines into alkylating reagents via Katritzky pyridinium salts. We report a complementary method that activates sterically encumbered α-3° primary amines through visible light photoredox catalysis. By condensing α-3° primary amines with electron-rich aryl aldehyde, we enable an oxidation and deprotonation event, which generates a key imidoyl radical intermediate. A subsequent β-scission event liberates alkyl radicals for coupling with electron-deficient olefins for the generation of unnatural γ-quaternary amino acids and other valuable synthetic targets.

Catalyst-Controlled C-H Functionalization of Adamantanes Using Selective H-Atom Transfer

A method for the direct functionalization of diamondoids has been developed using photoredox and H atom transfer catalysis. This C-H alkylation reaction has excellent chemoselectivity for the strong 3° C-H bonds of adamantanes in polyfunctional molecules.

Electrochemical radical reactions of alkyl iodides: a highly efficient, clean, green alternative to tin reagents

An electrochemical ‘redox-relay’ system has been developed which allows the generation of C-centered radicals. Intermolecular ‘tin-like’ radical reactions can subsequently be conducted under the most benign of conditions. The yields and efficiency of the processes are competitive and even superior in most cases to comparable conditions with tributyltin hydride. The use of air and electricity as the promotor (instead of a tin or other reagent) combined with the aqueous reaction media make this a clean and ‘green’ alternative to these classic C-C bond forming processes.

Catalyst-Free Decarboxylation of Carboxylic Acids and Deoxygenation of Alcohols by Electro-Induced Radical Formation

Electro-induced reduction of redox active esters and N-phthalimidoyl oxalates derived from naturally abundant carboxylic acids and alcohols provides a sustainable and inexpensive approach to radical formation via undivided electrochemical cells. The resulting radicals are trapped by an electron-poor olefin or hydrogen atom source to furnish the Giese reaction or reductive decarboxylation products, respectively. A broad range of carboxylic acid (1°, 2°, and 3°) and alcohol (2° and 3°) derivatives are applicable in this catalyst-free reaction, which tolerated a diverse range of functional groups. This method features simple operation, is a sustainable platform, and has broad application.

Photo-Mediated Decarboxylative Giese-Type Reaction Using Organic Pyrimidopteridine Photoredox Catalysts

The decarboxylative Giese-type reaction offers a versatile methodology for the radical alkylation of electron-deficient alkenes. Photo-mediated variants often require a pre-activation of carboxylic acids and/or employment of costly transition-metal photocatalysts. Herein, we present a metal-free photocatalyzed decarboxylative Giese-type addition to electron-deficient alkenes using pyrimidopteridine N-oxides as organic photoredox-active catalysts. This protocol comprises mono-, di-, and trisubstituted aliphatic, α-amino, and α-oxy acids as well as a variety of electron-deficient alkenes. Moreover, post-synthetic derivatization and applications are presented.

Silylated cyclohexadienes as new radical chain reducing reagents: Preparative and mechanistic aspects

Various silylated 1,4-cyclohexadienes are presented as superior tin hydride substitutes for the conduction of various radical chain reductions. Debrominations, deiodinations, and deselenations can be performed using these environmentally benign reagents. Furthermore, Barton - McCombie-type deoxygenations using silylated cyclohexadienes are described. Radical cyclizations, ring expansions, and Giesetype addition reactions with the new tin hydride substitutes are presented. The polymerization of styrene can be regulated using silylated cyclohexadienes. Rate constants for hydrogen atom abstraction from two 1-silyl-cyclohexadienes by primary C-radicals were determined. The effects of the cyclohexadiene substituents on the reaction outcomes are discussed. Finally, qualitative EPR experiments on silyl radical expulsion from silylated cyclohexadienyl radicals are presented.

Tetraaryldisilanes as a novel strategic radical reagent

Reactivity of 1,1,2,2-tetraaryldisilanes as a radical reagent in ethanol was studied in reduction of alkyl bromides, addition to olefins and alkylation onto heteroaromatic bases with alkyl bromides. The present organodisilanes showed moderate to good reactivities for these three types of radical reactions. Among some disilanes prepared, 1,1,2,2-tetraphenyldisilane is the most useful in view of its reactivity and ease of preparation.