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. Author manuscript; available in PMC: 2013 May 4.
Published in final edited form as: J Org Chem. 2012 Apr 24;77(9):4402–4413. doi: 10.1021/jo300551m

Table 1.

Optimization with Sodium Nitrite

graphic file with name nihms372639u2.jpg
entry solvent temperature reaction time (h) 11B NMR/GC/MS
1 EtOAc rt 48 S.M.
2 CH3CN rt 48 S.M.
3 heptane rt 48 S.M.
4 H2O rt 4 1a: protodeboronation (1:1)
5 EtOAc:H2O rt 4 1a: protodeboronation (3:1)
6 CH3CN:H2O rt 4 1a: protodeboronation (2:1)
7 heptane:H2O rt 4 1a
8 heptane:H2O 50 °C 2 1a (89% isolated yield)