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. Author manuscript; available in PMC: 2017 Dec 13.
Published in final edited form as: J Am Chem Soc. 2016 Sep 1;138(36):11690–11701. doi: 10.1021/jacs.6b05127

Table 1.

Model Studies for Alkene-Alkyne Coupling

graphic file with name nihms923594u2.jpg
Entrya Solvent (Conc.) 21 (equiv)b Convc 22:23c
1 CH2Cl2 (5 M) 1.2 0% - : -
2 DCE (5 M) 1.2 0% - : -
3 DMF (5 M) 1.2 33% 1 : 1
4 Acetone (5 M) 1.2 37% 3.5 : 1
5 Acetone (1 M) 5.0 56%d 4.0 : 1
a

All reactions were run using 0.1 mmol (20), and 10 mol% [CpRu(MeCN)3]PF6 at rt for 14 h.

b

21 was added as a solution drop-wise over 1h using a syringe pump.

c

Determined by 1H NMR.

d

Isolated yield.