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Synthesis of 6-n-alkylsalicylic acids (and isomeric acids…

AB - A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.

N2 - A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.

makes alkyl lithium and Grignard reagents excellent nucleophiles and useful reactants in synthesis.

Organolithium reagent - Wikipedia

Reduction of carbonyl compounds is another method of alcohol preparation. Aldehydes, ketones, esters and carboxylic acids can all be reduced, with the appropriate reagents, to alcohols. Catalytic hydrogenation or sodium borohydride is effective for aldehydes and ketones but not esters or carboxylic acids. Esters and acids are typically reduced with the stronger hydride reagent, lithium aluminum hydride. Thiols or mercaptans are the sulfur analogues of alcohols, containing an SH group, and can be synthesized by treating primary or secondary alkyl halides with excess NaSH, in an reaction. Thiols are more acidic than alcohols because the SH bond is weaker than the OH bond, and the conjugate base has more delocalization over the larger sulfur atom.

form a carbon-carbon bond, and the oxygen of the carbonyl compound or epoxide becomes an OH group. These methods all increase the carbon content of the alcohol to be synthesized. The typical organometallics used are Grignard reagents (RMgX), alkyl lithiums (RLi) and sodium alkynides. These reagents are also very strong bases and react with any OH or NH or alkynyl C-H in an acid-base reaction.

They are important reagents in organic synthesis, ..

Reduction of carbonyl compounds is another method of alcohol preparation. Aldehydes, ketones, esters and carboxylic acids can all be reduced, with the appropriate reagents, to alcohols. Catalytic hydrogenation or sodium borohydride is effective for aldehydes and ketones but not esters or carboxylic acids. Esters and acids are typically reduced with the stronger hydride reagent, lithium aluminum hydride. Thiols or mercaptans are the sulfur analogues of alcohols, containing an SH group, and can be synthesized by treating primary or secondary alkyl halides with excess NaSH, in an reaction. Thiols are more acidic than alcohols because the SH bond is weaker than the OH bond, and the conjugate base has more delocalization over the larger sulfur atom.

A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.

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caused by the bulky alkyl substituents ..


Grignard and Organolithium Reagents - Chemistry …

Syntheses of alcohols using organometallics involve the treatment of carbonyl compounds (aldehydes, ketones, esters and acyl halides) and epoxides with compounds which contain a carbon metal bond. The oppositely polarized carbons form a carbon-carbon bond, and the oxygen of the carbonyl compound or epoxide becomes an OH group. These methods all increase the carbon content of the alcohol to be synthesized. The typical organometallics used are Grignard reagents (RMgX), alkyl lithiums (RLi) and sodium alkynides. These reagents are also very strong bases and react with any OH or NH or alkynyl C-H in an acid-base reaction.

but Grignard and Alky Lithium ..

Organic chemistry: “”. How to make and alkyl (). Reactions of and alkyl (with solvents, and , and ). Synthesis problems—using radical , E2, SN2, oxidation (PCC), and for synthesis. The “” technique for solving synthesis problems.

Alkyl Halide Reactivity - Michigan State University

Organic chemistry: “”. of alcohols (PBr3, SOCl2). (, alkyl , ). Using the technique to solve synthesis problems involving (Gilman reagents).

Synthesis of phosphonates - Organic Chemistry Portal

Organic chemistry: “Introduction to amines”. Amine nomenclature. and of amines. Synthesis of amines—through SN2, through lithium aluminum hydride (LAH) reduction of amides or , through the Gabriel synthesis, or through reductive . Overview of LAH reductions—of and , of carboxylic acids, of esters, of amides, and of .

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