Nickel-Catalyzed Decarbonylative Amination of Carboxylic Acid Esters
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Abstract:
The reaction of carboxylic acid derivatives with amines to form amide bonds has been the most widely used transformation in organic synthesis over the past century. Its utility is driven by the broad availability of the starting materials as well as the kinetic and thermodynamic driving force for amide bond formation. As such, the invention of new reactions between carboxylic acid derivatives and amines that strategically deviate from amide bond formation remains both a challenge and an opportunity for synthetic chemists. This report describes the development of a nickel-catalyzed decarbonylative reaction that couples (hetero)aromatic esters with a broad scope of amines to form (hetero)aryl amine products. The successful realization of this transformation was predicated on strategic design of the cross-coupling partners (phenol esters and silyl amines) to preclude conventional reactivity that forms inert amide byproducts.Keywords:
Amide
Reactivity
Peptide bond
Primary (astronomy)
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In this paper,various common methods to preparing primary amine from carboxylic acid were systematically summarized.They included primary amine prepared through amidation of carboxylic acid,carboxylic acid firstly reduced to alcohol,ketone and aldehydes and followed by ammonolysis for preparing primary amine,and direct conversion of carboxylic acid.Meanwhile,the advantages and problems existing in each method were pointed out.Finally,the preparation of primary amine from carboxylic acid were prospected.
Primary (astronomy)
Primary alcohol
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To independently assess the contribution of ground-state pseudoallylic strain to the enormous rates of amide bond cleavage in tertiary amide derivatives of Kemp's triacid, we have studied four amide derivatives of (1α-3α-5β)-5-tert-butyl-1,3-cyclohexanedicarboxylic acid. Our results demonstrate that absent pseudoallylic strain, a 1,3-diaxial interaction of an amide with a carboxylic acid leads to only a 2400-fold increase in the rate of amide bond cleavage as compared with the rate of hydrolysis of an unactivated peptide bond.
Amide
Peptide bond
Cleavage (geology)
Bond cleavage
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Abstract The preparation of N,N-dibromo compounds by treatment of the parent amine or amide with free bromine,3 hypobromite solution,4 acetyl hypobromite5 or monobromoacetamide6 has been described. More recently, a method involving treatment of the free amide or amine with an N-bromo heterocycle, such as N-bromosuccinimide (NBS), has been developed.7 From our own experience, with the possible exception of the N-bromo amide or imide route, these methods tend to be highly specific, and cannot be reliably used as a general preparation of N,N-dibromoamines.
Amide
Imide
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A number of methods have been adopted for the synthesis of amides; among these methods, the oxidation of an amine to an amide is growing in interest as a means to prepare this imperative functional group.
Amide
Carbon fibers
Functional group
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In this work, new inhibitors of metal corrosion in sulfuric acid environments are studied depending on the duration of the process, inhibitor concentration and temperature. The main parameters for the synthesis of new metal corrosion inhibitors St.3 and St.12 grades using amine and amide containing organic substances are determined and methods for obtaining these inhibitors are described. The physicochemical properties of amine and amide containing organic inhibitors of corrosion and scaling in acidic process environments have been studied.
Amide
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During the study of the transpositions undergone by the amide of canphen-4-carboxylic acid on treatment with concentrated hydrochloric acid, the formation of the amide of 2-chlorobornan-4-carboxylic acid alone, arising in two polymorphous forms, has been confirmed. Its reduction produced 2-chloro-4-aminomethylbornane; the detachment of hydrochloric acid at the amide of canphen-1-carboxylic acid.
Amide
Hydrochloric acid
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By introduction of carboxylic acid amide groupings into 1-amino-adamantant (I), remarkable virustatic effects have been obtained, particularly which N-(1-adamantyl) cinnamic acid amide (VIIa) and N-(1-adamantyl)-3-(4'-methoxyphenyl)-acrylic acid amide (VIIc). The synthesis of the N-(1-adamantyl)-carboxylic acid amides (IV, VII, X) could be reallzed by interaction of I with carboxylic acids (II, V, VIII) via the carboxylic acid chlorides (III, VI, IX), the latter not being isolated for the simplification of the process.
Amide
Carbonic acid
Cinnamic acid
Acrylic acid
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Unconstrained amides that undergo fast hydrolysis under mild conditions are valuable sources of information about how amide bonds may be activated in enzymatic transformations. We report a compound possessing an unconstrained amide bond surrounded by an amino and a carboxyl group, each mounted in close proximity on a bicyclic scaffold. Fast amide hydrolysis of this model compound was found to depend on the presence of both the amino and carboxyl functions, and to involve a proton transfer in the rate-limiting step. Possible mechanisms for the hydrolytic cleavage and their relevance to peptide bond cleavage catalyzed by natural enzymes are discussed. Experimental observations suggest that the most probable mechanisms of the model compound hydrolysis might include a twisted amide intermediate and a rate-determining proton transfer.
Peptide bond
Amide
Cleavage (geology)
Bond cleavage
Limiting
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An efficient one-pot synthesis of 1-(4-bromophenyl)-1 H-tetrazol-5-amine was performed using 4-bromoaniline as the starting material. A novel and widely applicable amidation procedure was then employed, whereby 1-(4-bromophenyl)-1 H-tetrazol-5-amine was acylated with different acyl chlorides in the presence of lithium bis(trimethylsilyl)amide as catalyst, for the high-yield synthesis of [1-(4-bromophenyl)-1 H-tetrazol-5-yl]amide derivatives.
Amide
Trimethylsilyl
Lithium amide
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