Journal
ACS MEDICINAL CHEMISTRY LETTERS
Volume 11, Issue 4, Pages 597-604Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsmedchemlett.0c00093
Keywords
C(sp(2))-C(sp(3)) cross-coupling; parallel library synthesis; synthetic toolbox; photoredox catalysis; method comparison
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Funding
- Department of Education award, Minority Science and Engineering Improvement Program (MSEIP), Capacity Competitiveness Enhancement Model (CCEM) - Florida AM University [P120A160115]
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Despite recent advances in the field of C(sp(2))C(sp(3)) cross-couplings and the accompanying increase in publications, it can be hard to determine which method is appropriate for a given reaction when using the highly functionalized intermediates prevalent in medicinal chemistry. Thus a study was done comparing the ability of seven methods to directly install a diverse set of alkyl groups on drug-like aryl structures via parallel library synthesis. Each method showed substrates that it excelled at coupling compared with the other methods. When analyzing the reactions run across all of the methods, a reaction success rate of 50% was achieved. Whereas this is promising, there are still gaps in the scope of direct C(sp(2))-C(sp(3)) coupling methods, like tertiary group installation. The results reported herein should be used to inform future syntheses, assess reaction scope, and encourage medicinal chemists to expand their synthetic toolbox.
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