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. Author manuscript; available in PMC: 2016 Mar 11.
Published in final edited form as: J Am Chem Soc. 2015 Feb 27;137(9):3213–3216. doi: 10.1021/jacs.5b00344

Table 2. Optimization of Enantioselective 1,1-Arylborylationa,b.

graphic file with name nihms-720092-t0004.jpg
entry cat. solvent base additive ee (%) yield (%)
1 28 hexanes NaHCO3 – – <5
2 28 THF NaHCO3 – <5 72
3 28 Et2O NaHCO3 – 33 45
4 29 Et2O NaHCO3 – <5 14
5 27 Et2O NaHCO3 – 88 25
6 27 Et2O K2CO3 – 94 25
7 27 Et2O Na3PO4 – 93 26
8 27 Et2O Na3PO4 30a 70 40
9 27 Et2O Na3PO4 30b 90 39
a

Enantiomeric excess determined by chiral phase HPLC.

b

Yield determined by 1H NMR utilizing dimethyl sulfone as an internal standard.