- Modular Approach to 9-Monosubstituted Fluorene Derivatives Using MoV Reagents
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Oxidative coupling using molybdenum(V) reagents provides fast access to highly functionalized 9-monosubstituted fluorenes. This synthetic approach is highly modular, is high yielding, and tolerates a variety of labile moieties, e.g. amides or iodo groups. The established protocol leads to promising precursors for pharmacologically important analogues of melatonin.
- Franzmann, Peter,Trosien, Simon,Schubert, Moritz,Waldvogel, Siegfried R.
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supporting information
p. 1182 - 1185
(2016/03/15)
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- Pentaalkylstiboranes. 1. Synthesis of Homobenzylic Alcohols, Homoallylic Alcohols, Ethyl 5-Aryl-5-hydroxypent-2-enoates, and β-Hydroxypropionic Acid Derivatives via Pentaalkylstiboranes
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Although pentaalkylstiboranes have long been known, their applications in organic synthesis have not been exploited.It has been found that quaternary stibonium salts (n-Bu3SbCH2E)+X- (E = Ph, CH=CH2, CH=CHCO2Et, CO2Et, CN; X = Br, I, BPh4) on treatment with RLi (R = n-Bu, t-Bu, Ph) afford pentaalkylstiboranes, n-Bu3Sb(R)CH2E, which react with aromatic aldehydes to give, after subsequent hydrolysis, homobenzylic alcohols, homoallylic alcohols, ethyl 5-aryl-5-hydroxypent-2-enoates, and β-aryl-β-hydroxypropionitriles, respectively, in good to excellent yields.The reaction is chemoselective for aldehydes.
- Huang, Yao-Zeng,Liao, Yi
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p. 1381 - 1386
(2007/10/02)
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