Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 36, Pages 14126-14130Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b07960
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Funding
- Alexander von Humboldt foundation
- European Research Council ERC [692640]
- European Research Council (ERC) [692640] Funding Source: European Research Council (ERC)
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alpha-Functionalization of alkyl boronic esters and homologation of aryl boronic esters by regioselective radical C(sp(3))-H activation in boron-ate complexes is reported. Reaction of commercial or readily accessed aryl boronic acid pinacol esters with alkyl lithium reagents provides boron-ate complexes. Selective alpha-C-H abstraction by in situ generated trifluoromethyl radicals leads to radical anions that undergo electron transfer oxidation followed by 1,2-aryl/alkyl migration from boron to carbon to give the alpha-arylated/alkylated alkyl boronic esters. The valuable boronic ester functionality remains in the products and the cheap trifluoromethyl iodide acts as the oxidant in these C-C couplings. The 1,2-alkyl migration from boron to carbon is highly stereospecific allowing access to stereoisomerically pure boronic esters.
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