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. Author manuscript; available in PMC: 2019 Oct 31.
Published in final edited form as: J Am Chem Soc. 2018 Oct 16;140(43):14059–14063. doi: 10.1021/jacs.8b09191

Table 1.

Optimization of Reaction Conditionsa

graphic file with name nihms-1012512-t0005.jpg
Entry Deviation from standard condition Yield 12 (%)b Yield 13 (%)c
1 None 66 28
2 1 equiv of cyclohexane 44 33
3 no photocatalyst  0 48
4 no ligand  3 27
5 no nickel  0 17
6 no light  0 34
7 26 °C 46 17
8 40 °C 55 32
9 no Na2WO4·2H2Od 39 19
10 no Na2WO4·2H2Od, 72 h 62 22
11 Na2SiO3·5H2O instead of Na2WO4·2H2O 57 25
12 no K3PO4d 58 35
13 no K3PO4, no Na2WO4·2H2O 17 11
a

K3PO4 (2 equiv); Na2WO4·2H2O (1 equiv).

b

Yields determined by 1H NMR using 4-fluoroanisole as an external standard.

c

Yield determined by GC analysis based on consumption of 2 equiv of chloroformate for production of 1 equiv of DPC.

d

3 equiv of base used.