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. Author manuscript; available in PMC: 2019 Jul 3.
Published in final edited form as: J Am Chem Soc. 2018 Apr 20;140(17):5701–5705. doi: 10.1021/jacs.8b02834

Table 1.

Control Experiments for the Alkyne Hydroalkylationa

graphic file with name nihms-1023791-t0004.jpg
entry conditions yield r.r.
1 1.0 equiv TMG 17% >20:1
2 0.1 equiv TMG 80%(80%)b >20:1
3 no light 0% –
4 no photocatalyst 0% –
5 no Ni catalyst <5% –
6 4-CzIPN catalystc 70% >20:1
a

Performed with H2O (20 equiv), carboxylic acid (1.0 equiv), and 1-heptyne (1.3 equiv). Yields by 1H NMR.

b

Yields in parentheses are isolated.

c

4-CzIPN (2 mol %) used in place of Ir catalyst.