The Synthetic Routes of 1,4,7,10-Tetra(tert-butyl)perylene

The synthesis of 1,4,7,10-tetra(tert-butyl)perylene is a challenging task in the chemical industry.
This is a highly sought-after molecule due to its unique properties and potential applications in a wide range of fields, including materials science, optoelectronics, and energy storage.
There are several synthetic routes available to obtain this molecule, and each route has its own advantages and challenges.

One of the most commonly used synthetic routes to 1,4,7,10-tetra(tert-butyl)perylene is the reaction of 4,4',4''-trimethyl-2,2'-bipyridine with 2,3-dimethyl-5,6-dibromopyridine.
This reaction results in the formation of the corresponding bipyridine dicarboxylate, which can then be hydrolyzed to yield the tetrasubstituted perylene.
This route offers several advantages, such as high yield and purity of the desired product, and straightforward work-up procedures.

Another synthetic route to 1,4,7,10-tetra(tert-butyl)perylene involves the reaction of 2,2'-bipyridine with 2,3-dimethyl-5,6-dibromopyridine in the presence of a Lewis acid catalyst.
This reaction leads to the formation of the corresponding bipyridine diester, which can be dehydrated to yield the tetrasubstituted perylene.
This route offers several advantages, such as mild reaction conditions, high yield and purity of the desired product, and ease of work-up procedures.

A less common but highly promising synthetic route to 1,4,7,10-tetra(tert-butyl)perylene is the Pd-catalyzed cross-coupling reaction between 2-butyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9(10H)-one and 2-bromo-1,4,7,10-tetraoxacyclopentadecane.
This reaction results in the formation of the corresponding cross-coupled product, which can be hydrolyzed to yield the tetrasubstituted perylene.
This route offers several advantages, such as high yield and purity of the desired product, and the potential for metal-free and highly chemoselective synthesis.

In conclusion, the synthetic routes to 1,4,7,10-tetra(tert-butyl)perylene are numerous and varied, each with its own advantages and challenges.
The three routes outlined here are but a few examples of the many methods that have been developed in the chemical industry to synthesize this important molecule.
The continued development and refinement of these routes is likely to result in even more efficient and cost-effective syntheses of this valuable molecule, with potential applications in a wide range of fields.