Modular Synthesis of Triarylmethanes through Palladium‐Catalyzed Sequential Arylation of Methyl Phenyl Sulfone

Abstract

Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed CÀH arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane-based materials and pharmaceuticals.

Hydride Reduction by a Sodium Hydride–Iodide Composite

“…Thep resent protocol is suitable for the facile construction of tertiary carbon centers of monoaryl (products 3b-p), diaryl (products 3q-u), and even triaryl methanes (products 3v and 3w)from the corresponding carbonitriles,t hus offering an ew retrosynthetic strategy to access this class of compounds. [8] Notably, this method allows the preparation of cycloalkyl arenes (products 3j-p)p ossessing strained cyclobutyl (products 3m and 3n)and tetrahydropyranyl moieties (product 3o)aswell as 2-cyclohexylpyridine (3p)w ith high efficiency. It was observed that an electron-rich 4-methoxyphenyl group rendered the reaction rate of the decyanation slower (3j vs. 3k and 3m vs. 3n).…”