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. 2010 Apr 6;1(4):165–169. doi: 10.1021/ml100013s

Scheme 5. Synthesis of Benzoxaboroles with NH and CH2 Linkage Groups.

Scheme 5

Reagents and conditions: (a) CuI, l-proline, t-BuONa, DMSO, 50 °C. (b) LiHMDS, Boc2O, THF, −80 °C to room temperature. (c) NBS, Bz2O2, CCl4, reflux. (d) NaOAc, DMF, 70 °C. (e) NaOH, MeOH−H2O, reflux. (f) DHP, pyridine, p-TsOH, CH2Cl2. (g) n-BuLi, B(iPrO)3, −78 °C to room temperature. (h) p-TsOH, pyridine, EtOH, 50 °C. (i) TFA, CH2Cl2, 0 °C to room temperature. (j) Pd(dppf)Cl2, CsF, K2CO3, dioxane, 80 °C. (k) CeCl3, NaI, CH3CN, reflux. (l) Tf2O, Et3N, CH2Cl2, −78 °C. (m) Bis(pinacol-diboron), Pd(dppf)Cl2, KOAc, dioxane, 80 °C. (n) NaBH4, MeOH−THF, 0 °C. (o) HCl.