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- W2330601045 abstract "Titanocene bis(catecholborane), [Cp2Ti(HBcat)2] (1), catalyzes the room-temperature hydroboration of carbonyl compounds by pinacolborane (HBpin) rapidly, cleanly, and chemoselectively. Aryl aldehydes and ketones produced alkoxypinacolboronate esters in moderate to high yields in 2 h, and facile hydrolysis of alkoxypinacolboronate esters over silica occurred cleanly to afford alcohols in good yields. Complex 1 demonstrated a preference for C═O bonds over C═C bonds in both conjugated and nonconjugated enones. Kinetic studies of the catalytic hydroboration of a series of acetophenones showed that electron-poor substrates undergo the reaction more quickly than electron-rich substrates. This result is consistent with the proposed mechanism, in which stronger π-acids should undergo C═O bond cleavage more readily. Computational studies using benzophenone and benzaldehyde showed that the hydroboration is spontaneous and likely proceeds via intermediates that are best described as Ti metallacycles whose structures are not significantly altered by substrate steric differences. This result indicates that similarities in the electronic properties of benzophenone and benzaldehyde supersede their steric differences in determining reaction outcomes." @default.
- W2330601045 created "2016-06-24" @default.
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- W2330601045 date "2012-12-19" @default.
- W2330601045 modified "2023-10-18" @default.
- W2330601045 title "Titanocene(II)-Catalyzed Hydroboration of Carbonyl Compounds" @default.
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- W2330601045 doi "https://doi.org/10.1021/om300828m" @default.
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