Simple and Economical Preparation of Aminoboranes for Use in Organic Synthesis

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2020-RAMA-68862
Researchers at Purdue University have developed a new method of preparing aminoboranes for use as reagents in organic synthesis, including the preparation of aryl- and alkenylboronate esters as Suzuki coupling partners. Suzuki coupling reactions are important in the development of pharmaceuticals; however, current methods for synthesizing the necessary boronate esters often require the use of toxic, corrosive, and expensive reagents. Purdue researchers have introduced iodine as a safe and cost-effective reagent to covert amine-boranes to aminoboranes in nearly quantitatively yield with high purity. This protocol demonstrated broad tolerance toward other chemical functionality during the preparation of a series of boronate esters, which were isolated in 75-95% yield.

Potential Applications:
-Pharmaceuticals
-Life Science Research
-Materials Chemistry

Advantages:
-Economical route to the preparation of arylaminoboranes and other Suzuki coupling arylboron
partners
-Does not require use of toxic or corrosive reagents
-Simple
-Cost Effective
-High Yield
-High Purity

The system was validated by preparing iodoboranes, aminoboranes, and aryl(dialkylamine)boranes from amine-boranes. Then, each of the following compounds were synthesized: aryl boronates with 95% yield, amino-iodoboranes with 75% yield, aminoboranes from sodium borohydride with 75% yield, aryl(dialkylamine)boranes from sodium borohydride with 75% yield, and aryl boronates from sodium borohydride with up to 95% yield.
Aug 21, 2020
Provisional-Patent
United States
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Purdue Office of Technology Commercialization
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