Concepedia

Amidophosphine Boranes as Hydroboration Reagents for Nitriles, Alkynes, and Carboxylic Acids

Ravi Kumar, Rohan Kumar Meher, Jyoti Sharma, Abhijit Sau, Tarun K. Panda

Organic Letters · 2023 · 12 citations · 38 references

DOI

Abstract

We report here the hydroboration of nitriles, alkynes, and carboxylic acids using amidophosphine boranes {(BH<sub>3</sub>)(PPh<sub>2</sub>)-NC(CH<sub>3</sub>)<sub>3</sub>}, {(BH<sub>3</sub>)<sub>2</sub>(PPh)<sub>2</sub>N(CH<sub>2</sub>)C<sub>6</sub>H<sub>5</sub>}, and {(BH<sub>3</sub>)<sub>2</sub>(PPh<sub>2</sub>)<sub>2</sub>N-(BH<sub>3</sub>)CH<sub>2</sub>C<sub>6</sub>H<sub>4</sub>N} as reducing agents. These compounds were synthesized to replace more commonly used borane reagents. Solid amidophosphine boranes, which were synthesized with ease, demonstrated excellent reactivity and functional group tolerance toward a wide variety of nitriles, alkynes, and carboxylic acids, affording the corresponding ammonium salts, alkenes, and alcohols in good yield.

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