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. Author manuscript; available in PMC: 2015 Jan 8.
Published in final edited form as: Chem Sci. 2011 May 16;2(8):1606–1610. doi: 10.1039/C1SC00235J

Table 3.

Optimization for Large Scale Reactions

graphic file with name nihms640993u3.jpg
Entry Scale (mmol) Catalyst (mol %) Conc. (M) Cu(OAc)2•H2O (mol %) GC/MS yield (%)
1 .22 5 0.3 20 86
2 .22 1 0.3 20 15
3a .22 1 0.3 20 37
4a .22 2.5 0.15 20 35
5a .44 1 0.6 20 45
6a 6.22 2 0.6 20 69b
7c .22 5 .3 0 40
a

Portionwise addition of alkyne; see SI.

b

Isolated yield.

c

Reaction conducted under O2 in presence of NaOAc (4 equiv).