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. Author manuscript; available in PMC: 2016 Sep 21.
Published in final edited form as: Angew Chem Int Ed Engl. 2015 Jul 24;54(39):11424–11427. doi: 10.1002/anie.201504076

Table 3.

Scope of alkynes in the [4+2] annulation.

graphic file with name nihms732628u4.jpg
Entry[a] Substrate Alkyne Product t [h] Yield[%][b]
1 1a graphic file with name nihms732628t13.jpg
2b
graphic file with name nihms732628t14.jpg
5a
16 71
2[c] 1a graphic file with name nihms732628t15.jpg
2c
graphic file with name nihms732628t16.jpg
5b
16 57
3 1j 2b graphic file with name nihms732628t17.jpg
5c
16 72
4 1f graphic file with name nihms732628t18.jpg
2d
graphic file with name nihms732628t19.jpg
5d
14 42
5 1a graphic file with name nihms732628t20.jpg
2e
graphic file with name nihms732628t21.jpg
5e
12 66
6 graphic file with name nihms732628t22.jpg
2f
graphic file with name nihms732628t23.jpg
5f
14 61
7 1h graphic file with name nihms732628t24.jpg
2g
graphic file with name nihms732628t25.jpg
5g
24 42
8 1c graphic file with name nihms732628t26.jpg
2h
graphic file with name nihms732628t27.jpg
5h
12 92
[a]

Reaction condition: substrate (0.2 mmol, 0.1 M in degassed MeOH), 2b2h (0.6 mmol), 4a (2 mol%), irradiation with two 18 W LED light bulbs.

[b]

Yield of the isolated product.

[c]

Mixed solvent of MeOH and CH3NO2 (1:1).