Synthesis
General procedure for the synthesis of 1-(3-bromophenyl)ethanol and (S)-1-(3-bromophenyl)ethanol from 3'-bromoacetophenone: under dry argon protection, the catalyst [0.4 mol% (complexes 12-22) or 0.2 mol% (dinuclear complex 24)] and 3'-bromoacetophenone (2.5 mmol) were added to a three necked Schlenk flask. The mixture was stirred at 82 °C for 15 min before adding 5 mL of a 0.06 M solution of base (Cs2CO3) in 2-propanol (0.3 mmol). The reaction progress was monitored by an HP-6890 gas chromatograph. In all reactions, only the corresponding alcohols and ketones were detected as products. Conversion rates and enantiomeric excess values (e.e. values) were determined by gas chromatography using a Supelco β-DEX 120 chiral capillary column.
References
[1] Molecular Catalysis, 2018, vol. 456, p. 75 - 86
[2] Tetrahedron Letters, 2018, vol. 59, # 8, p. 719 - 722
[3] Angewandte Chemie, 1995, vol. 107, # 18, p. 2165 - 2166
[4] Angewandte Chemie, 1995, vol. 107, # 18, p. 2165 - 2166
[5] Journal of Organometallic Chemistry, 1997, vol. 547, # 1, p. 97 - 101
