Functionalization of Heteroalkenes and Arenes into Valuable Amines

Selectively and Directly Functionalizes Hydrocarbons into Amines, Enhancing Reactivity and Versatility

This transformation process selectively and directly functionalizes hydrocarbons into amines without harsh conditions, expensive reagents, or unnecessary waste generation. Low molecular weight alkyl and aryl amines are among the highest-volume amines utilized in the chemical industry, serving as essential materials for pharmaceuticals, polymers, dyes, and other applications. However, common amine formation techniques require harsh conditions, costly reagents or catalysts, and are highly energy intensive. This hinders the development of new materials, drugs, and energy-related technologies. Furthermore, low product selectivity in these methods leads to excessive waste and emissions. There is a need for a cost-efficient method to convert readily available small-molecule feedstock into valuable amine-based products. This need is further reinforced by the size of the market: the global amines market was valued at USD 17.1B in 2023 and is projected to reach USD 23.8B by 2030, at a CAGR of 4.8%.

Researchers at the University of Florida have developed a process for the selective and direct conversion of hydrocarbons into amines. Building on a broader platform for the functionalization of heteroalkanes and arenes, this low-temperature, low-pressure, and sustainable approach operates under mild conditions and does not require superacids or expensive catalysts. By using an oxidizing reagent containing a nitrogen-based ligand, this method enables the production of valuable amines through a single-step mechanism, increasing reaction selectivity and reducing waste and emissions.

Application

Selective and direct functionalization of hydrocarbons into amines for use in various industries, such as pharmaceuticals, polymers, and dyes

Advantages

• Functionalizes complex molecules into nitrogen-functionalized products, enhancing their reactivity and enabling further transformation into versatile compounds, such as amines
• Provides a single transition-state mechanism, increasing efficiency by forming new bonds in one step
• Prevents formation of unstable reaction intermediates, increasing selectivity, reducing by-products and waste, and eliminating the need for expensive catalysts or reagents, minimizing capital expenses
• Uses an oxidizing electrophile as reagent, increasing the process’ sustainability through the ability to recycle the reagent from its reduced form
• Operates under mild conditions, lowering energy consumption and reducing operational costs
• Provides a versatile reaction platform, enabling heteroalkane functionalization for efficient amine production and offering potential to be extended to other chemical transformations

Technology

This process enables the selective and direct conversion of hydrocarbons into nitrogen-functionalized products, such as amines. It builds on a broader platform for the functionalization of heteroalkanes and arenes using emerging oxidizing electrophiles under mild conditions, without the need for superacids or catalysts. In this general process, hydrocarbons react with an oxidizing reagent, to produce an initial reaction product. This intermediate then reacts with a weaker acid solvent to yield a variety of functionalized compounds. Specifically, when the oxidizing electrophile contains a nitrogen-based ligand, this reaction produces a nitrogen-functionalized product and a reduced form of the reagent, with the valuable amine products readily isolated.