Chan-Evans-Lam Amination of Boronic Acid Pinacol …

Aerobic, Medal Mediated Ketone Synthesis from Thiol Esters and Boronic Acids
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The Chan–Evans–Lam reaction is a valuable C–N bond forming process

The Chan–Evans–Lam reaction is a valuable C–N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan–Evans–Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found to enable effective C–N bond formation using aryl amines while EtOH is not required for the coupling of alkyl amines.

Also disclosed herein are novel boronic ester and acid compounds, their synthesis and uses
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Other researchers are exploiting the well known strong and reversible complexation between boronic acids and diol (1,2 or 1,3)-containing compounds. By forming transient esters with these kinds of alcohols, boronic acids can act as catalysts or templates for directed reactions. For example, Yamamoto and co-workers discovered that several electron poor arylboronic acids, in particular 3,4,5-trifluorobenzeneboronic acid, catalyzes amidation reactions between carboxylic acids and amines. (8) Aryl boronic acids also catalyze the alkaline conversion of D-glucos to D-fructose. (9)

Disclosed herein are boronic ester and acid compounds, their synthesis and uses
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To support clients conducting Suzuki-Miyaura cross-coupling reactions for biaryl synthesis, as well as other synthesis reactions, ARCI stocks boronic acid/ester intermediates. Our catalogue includes many novel and rare intermediates, available in a range of standardized quantities.

Synthesis of Boronic Acids and Esters from Pinacolborane and Aminoborane Under Ambient Magnesium-, Iodine-, and Zinc-Mediated Conditions
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