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. Author manuscript; available in PMC: 2019 Oct 24.
Published in final edited form as: J Am Chem Soc. 2018 Oct 10;140(42):13703–13710. doi: 10.1021/jacs.8b07064

Table 1.

Reaction Condition Optimizationa

graphic file with name nihms-993041-t0002.jpg

entry (2/3/1) solvent T (°C), t (h) yield (%)b
1 1/2/2 THF 0, 30 44
2 1/2/2 Et2O/THF (20/1) 0, 30 29
3 1/2/2 Et2O 0, 30 48
4 1/2.5/2 Et2O 0, 30 40
5 1/1.5/2 Et2O 0, 30 41
6 1/2/3 Et2O 0, 30 67
7 1/2/3 Et2O 25, 30 61
8 1/2/3 Et2O −78, 30 trace
a

Aryne precursor (0.25 mmol), solvent (1.5 mL).

b

Yields determined by GC analysis with n-decane as an internal standard.