Abstract
Development of a CuCl/phosphine system to catalyze phenylation and methylation of <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mi>N</mml:mi></mml:math>-tosyl aldimines with phenylboronic and methylboronic acids
Highlights
In many essential chemical or biological reactions, various amines containing phenyl or methyl groups are utilized as precursors for preparing drugs and biological compounds as well as ligands in organic synthesis [1,2]
The use of air-stable organoboron reagents is preferred compared to zinc, tin [7,8], silane [9], and titanium [10], which are toxic and difficult to manage
Hu and co-workers reported the addition of CuCl/bipyridine-catalyzed arylboroxines to N -Ts-aldimines using microwave energy, achieving a conversion rate up to 84% [23]
Summary
In many essential chemical or biological reactions, various amines containing phenyl or methyl groups are utilized as precursors for preparing drugs and biological compounds as well as ligands in organic synthesis [1,2]. When the model reaction is performed by using triphenylboroxine (2b) with many different catalytic systems and conditions, the same result is produced (up to 40% yield; entry 18, Table 2). The former is more active and produces an adduct in less time. Noncoordinate bases such as potassium carbonate do not efficiently promote the reaction, while triethylamine together with potassium carbonate as an additive increases both the yield and the rate significantly (entries 15 and 16, Table 2) Much stronger bases such as potassium fluoride and potassium hydroxide (2:1 ratio to boron reagent) convert aldimine to the required product with a 90% yield. The coordination of copper(I) chloride with PPh3 was determined as the most efficient combination for this addition, delivering the desired products in moderate-
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