Abstract
Regiodivergent 1,2-hydroboration of 1,3-dienes with pinacolborane has been accomplished by well-defined cobalt complexes of different bidentate ligands. The iminopyridine-cobalt system is selective for Markovnikov 1,2-hydroboration to form allylboronates, while the FOXAP-cobalt (FOXAP=(S)-1-(diphenylphosphino)-2-[(S)-4-isopropyloxazolin-2-yl]ferrocene) catalyst effects the complementary anti-Markonikv 1,2-hydroboration to afford homoallyboronates with high regioselectivity.
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When chiral ligands L2, L3, L4 were used, the ee values of the allylboronate product 2a were checked by chiral HPLC, indicating low enantioselectity with 2% ee for L2, 3% ee for L3 and 22% ee for L4
Acknowledgements
This work was supported by the National Key R&D Program of China (2016YFA0202900, 2015CB856600), the National Natural Science Foundation of China (21825109, 21432011, 21572255, 21732006), Chinese Academy of Sciences (XDB20000000, QYZDB-SSW-SLH016), and Science and Technology Commission Shanghai Municipality (17JC1401200).
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Peng, S., Yang, J., Liu, G. et al. Ligand controlled cobalt catalyzed regiodivergent 1,2-hydroboration of 1,3-dienes. Sci. China Chem. 62, 336–340 (2019). https://doi.org/10.1007/s11426-018-9418-7
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DOI: https://doi.org/10.1007/s11426-018-9418-7