Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 17, Pages 4279-4282Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201800527
Keywords
alkylation; boron; heterocycles; metallate rearrangement; photoredox catalysis
Categories
Funding
- University of Bristol
- ERC [670668]
- EPSRC [EP/I038071/1]
- EU [744242]
- Swiss National Science Foundation [P2EZP2175145]
- BBSRC [BB/F011539/1] Funding Source: UKRI
- EPSRC [EP/K03927X/1, EP/L011999/1, EP/I038071/1] Funding Source: UKRI
- Biotechnology and Biological Sciences Research Council [BB/F011539/1] Funding Source: researchfish
- Engineering and Physical Sciences Research Council [EP/I038071/1, EP/K03927X/1, EP/L011999/1] Funding Source: researchfish
- European Research Council (ERC) [670668] Funding Source: European Research Council (ERC)
- Marie Curie Actions (MSCA) [744242] Funding Source: Marie Curie Actions (MSCA)
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Furan- and indole-derived boronate complexes react with alkyl iodides under radical (photoredox) or polar (S(N)2) conditions to generate three-component alkylation products with high efficiency and complete stereospecificity. The methodology allows the incorporation of versatile functional groups such as nitriles, ketones, esters, sulfones, and amides, providing rapid access to complex chiral heteroaromatic molecules in enantioenriched form. Interestingly, while indolyl boronate complexes react directly with alkyl halides in a polar pathway, furyl boronates require photoredox catalysis. Careful mechanistic analysis revealed that the boronate complex not only serves as a substrate in the reaction but also acts as a reductive quencher for the excited state of the photocatalyst.
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