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• W2894655722 endingPage "5330" @default.
• W2894655722 startingPage "5323" @default.
• W2894655722 abstract "Abstract A series of chiral bioinspired Mn‐aminopyridine complexes of the type [L*Mn II (OTf) 2 ] (where L* is 2,2′‐bipyrrolidine derived ligand, bearing trifluoroalkoxy and alkyl substituents) have been tested as catalysts in benzylic C−H hydroxylation of arylalkanes with H 2 O 2 in fluorinated ethanols media. In 2,2,2‐trifuoroethanol, the yield of the target ethylbenzene oxidation product, chiral 1‐phenylethanol, reaches 45 %, which is much better than in the common solvent CH 3 CN (5‐6 %). The selectivity for 1‐phenylethanol formation increases in the following order: CH 3 CN<2‐fluoroethanol<2,2‐difluoroethanol<2,2,2‐trifuoroethanol, while 2,2‐difluoroethanol ensures the highest asymmetric induction in this series, affording chiral benzylic alcohols with up to 89 % ee . In trifluoroethanol, the observed primary k H / k D value of 2.3 has been measured for the oxidation of 1‐phenylethanol/ α ‐D‐1‐phenylethanol, which is similar to that in CH 3 CN (2.2). At the same time, depending on the solvent, CH 3 CN or 2,2,2‐trifuoroethanol, the oxidations of 1‐phenylethanol demonstrates drastically different linear free‐energy relationships; possible effect of the hydrogen‐bond donor (HBD) nature of CF 3 CH 2 OH is discussed in this context. Noticeably, it has been shown that by switching the absolute chirality (( S , S )− or ( R , R )−) of the catalyst, the oxidation of complex substrate of natural origin, estrone acetate, can be diverted to predominant formation of either the tertiary C9‐alcohol or of the C6‐ketone, respectively." @default.
• W2894655722 created "2018-10-12" @default.
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• W2894655722 date "2018-11-05" @default.
• W2894655722 modified "2023-10-16" @default.
• W2894655722 title "Enantioselective Benzylic Hydroxylation of Arylalkanes with H₂O₂ in Fluorinated Alcohols in the Presence of Chiral Mn Aminopyridine Complexes" @default.
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• W2894655722 doi "https://doi.org/10.1002/cctc.201801476" @default.
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