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. Author manuscript; available in PMC: 2025 Jul 24.
Published in final edited form as: J Am Chem Soc. 2024 Jul 16;146(29):19696–19703. doi: 10.1021/jacs.4c07125

Table 1.

Conditions Explored for Reaction Optimizationa

graphic file with name nihms-2018965-t0005.jpg
Entry Additive Yield of 1b Yield of 1c
1 none 14% 18%
2 THF 13% 12%
3 18-crown-6 3% 2%
4 Ph3N 9% 13%
5 pyridine 7% 9%
6 1,10-phen 9% 1%
7 HMPA 9% 8%
8 benzophenone 32% ND
9 benzophenoneb 57% 2%
10 c benzophenone 72% 2%
a

Optimization was conducted on a 0.1 mmol scale. Yield was determined by 1H NMR using mesitylene internal standard.

b

0.25 equiv of benzophenone.

c

2.5 equiv of TEMPO+PF6, 2.25 equiv of KHMDS, 0.45 equiv of benzophenone.