Repurposing the novel DATB catalyst for the direct catalytic cross-coupling of carboxylic acids

2022 Fiscal Year Final Research Report

• Project/Area Number: 20K15292
• Research Category: Grant-in-Aid for Early-Career Scientists
• Allocation Type: Multi-year Fund
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: Microbial Chemistry Research Foundation
• Principal Investigator: Opie Christopher 公益財団法人微生物化学研究会, 微生物化学研究所, 研究員 (90858531)
• Project Period (FY): 2020-04-01 – 2023-03-31
• Keywords: DATB / Catalyst / Boron / Amide bond / Synthesis

Outline of Final Research Achievements

We had initially anticipated that the DATB catalyst could be used in tandem with transition metals to access novel reaction pathways. However. despite countless attempts over the course of a year, we we never successful in achieving this goal. As such, we changed modified our plan to exploring how changes to the structure of DATB could alter its reactivity. One of our ideas was to synthesize, characterize and test the catalytic activity of N(BOH)2-containing molecules. While this moiety is structurally similar to DATB, no synthetic pathways to produce it were present in the literature. Fortunately, we were successful in our endevour, producing a shelf-stable compound that was even more catalytically active than the DATB catalyst. The work was published in Org. Lett. (2023, 25, 4, 694-697). This novel catalytically-active moiety likely
provides a novel mode of action for amide activation, which warrants further investigation.

Free Research Field

Catalysis

Academic Significance and Societal Importance of the Research Achievements

One of the most frequently encountered reactions in chemistry, especially in medicinal chemistry, is that of amide bond formation. The 'traditional' methods to achieve this transformation necessarily occur with concurrent production of waste materials. This project uncovered a new catalytic method.