Journal
CHEMICAL SCIENCE
Volume 12, Issue 20, Pages 7066-7072Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc01349a
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Funding
- NSF [CHE-1902509]
- Merck
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In this study, a new three-component reaction was reported for the synthesis of benzylamine bicyclo[1.1.1]pentane pinacol boronates, demonstrating the versatility of boronate esters and their successful application to challenging tertiary pinacol boronates.
We report a 3-component reaction between N-benzyl ketimines, [1.1.1]propellane, and pinacol boronates to generate benzylamine bicyclo[1.1.1]pentane (BCP) pinacol boronates. These structures are analogous to highly sought diarylmethanamine cores, which are common motifs in bioactive molecules. We demonstrate the versatility of the boronate ester handle via downstream functionalization through a variety of reactions, including a challenging Pd-catalyzed (hetero)arylation that exhibits a broad substrate scope. Together, these methods enable the synthesis of high-value BCP benzylamines which are inaccessible by existing methods. Furthermore, we demonstrate the successful application of these newly developed (hetero)arylation conditions to a variety of challenging tertiary pinacol boronates, including nitrogen-containing heterocycles, 1,1-disubstituted cyclopropanes, and other BCP cores.
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