Boryl Radical-Promoted Dehydroxylative Alkylation of 3-Hydroxyoxindole Derivatives.
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DOI: 10.1021/acs.orglett.3c00521
Abstract: A boryl radical-promoted dehydroxylative alkylation of 3-hydroxy-oxindole derivatives is achieved. The reaction starts from addition of 4-dimethylaminopyridine (DMAP)-boryl radical to the amide carbonyl oxygen atom, which induces a spin-center shift process to promote the C-O… read more here.
Keywords: radical promoted; alkylation hydroxyoxindole; dehydroxylative alkylation; promoted dehydroxylative ... See more keywords
Synthesis of Polysubstituted Cyclohexenes via Pyridine-Boryl Radical-Catalyzed Formal [4 + 2] Cycloadditions of Cyclobutanes with Alkynes.
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DOI: 10.1021/acs.orglett.5c02553
Abstract: Polysubstituted cyclohexene derivatives widely exist in pharmaceuticals and bioactive natural products. Herein, we report the first pyridine-boryl radical-catalyzed intermolecular formal [4 + 2] cycloadditions between cyclobutanes and alkynes, producing tri- and tetrasubstituted cyclohexene derivatives with… read more here.
Keywords: formal cycloadditions; cycloadditions cyclobutanes; cyclobutanes alkynes; pyridine boryl ... See more keywords
Halogen Atom Transfer-Induced Homolysis of C-F Bonds by the Excited-State Boryl Radical.
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DOI: 10.1021/jacs.4c06337
Abstract: A novel reactivity toward C-F bond functionalization has been developed, which could be designated as fluorine atom transfer (FAT). A photoexcited state of an N-heterocyclic carbene-ligated boryl radical exhibits a transcendent reactivity, capable of activating… read more here.
Keywords: homolysis; state; atom transfer; boryl radical ... See more keywords
Photoredox-Catalyzed Cyclopropanation via Ligated Boryl Radical-Mediated Nonstabilized Carbene Formation.
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DOI: 10.1021/jacs.5c12677
Abstract: The [2 + 1] cycloaddition of carbenes with alkenes is widely regarded as one of the most straightforward strategies for synthesizing cyclopropanes, which are ubiquitous motifs in pharmaceuticals. A significant challenge in cyclopropanation reactions is… read more here.
Keywords: nonstabilized carbene; boryl radical; ligated boryl; cyclopropanation ... See more keywords