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Amide coupling is one of the most common reactions in organic chemistry and DMTMM is one reagent used for that reaction. The mechanism of DMTMM coupling is similar to other common amide coupling reactions involving activated carboxylic acids. [1] Its precursor, 2-chloro-4,6,-dimethoxy-1,3,5-triazine (CDMT), has also been used for amide coupling.
A similar reaction involving thiols and selenols can yield the corresponding esters. [6] The alcohol reaction can also be used to form glycosidic bonds. [7] Similarly, an acid can be used in the place of an alcohol to form the anhydride, although dicyclohexylcarbodiimide is a more typical reagent.
The scheme above shows the general mechanistic steps for EDC-mediated coupling of carboxylic acids and amines under acidic conditions. The tetrahedral intermediate and the aminolysis steps are not shown explicitly. EDC couples primary amines, and other nucleophiles, [5] to carboxylic acids by creating an activated ester leaving group. First ...
BOP (benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate) is a reagent commonly used for the synthesis of amides from carboxylic acids and amines in peptide synthesis. [1] [2] It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions. [3]
The reaction mechanism is described as follows: . With amines, the reaction proceeds without problems to the corresponding amides because amines are more nucleophilic.If the esterification is slow, a side-reaction occurs, diminishing the final yield or complicating purification of the product.
In one important reaction type, a main group organometallic compound of the type R-M (where R = organic group, M = main group centre metal atom) reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction. [1] [2] [3]
In organic chemistry, an amide, [1] [2] [3] also known as an organic amide or a carboxamide, is a compound with the general formula R−C(=O)−NR′R″, where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms.
Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important reaction type is this: R−M + R'−X → R−R' + MX (R, R' = organic fragments, usually aryl; M = main group center such as Li or MgX; X = halide) These reactions are used to form carbon–carbon bonds but ...