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. Author manuscript; available in PMC: 2014 Apr 4.
Published in final edited form as: Chem Commun (Camb). 2013 Apr 4;49(26):2616–2618. doi: 10.1039/c3cc40634b

Table 2.

Rh-Catalyzed [5 + 2] Cycloaddition of 5c and Alkynes (Ar = p-Me2NC6H4)a

graphic file with name nihms449166e2.jpg (3)
graphic file with name nihms449166e3.jpg (4)
Entry Alkyne Substrates Yield Ratio of (9: 9′)
1 7 6c, 97% only 6c
2 8a, graphic file with name nihms449166t1.jpg 9a, 87% only 9a
3 8b, graphic file with name nihms449166t2.jpg 9b, 89% >20:1
4 8c, graphic file with name nihms449166t3.jpg 9c, 95% only 9c
5 8d, graphic file with name nihms449166t4.jpg 9d, 96% 17:1
6 8e, graphic file with name nihms449166t5.jpg 9e, 74% only 9e
7b 8f, graphic file with name nihms449166t6.jpg 9f, 58% >20:1
8c 8g, graphic file with name nihms449166t7.jpg 9g, 77% 8:1
9 8h, graphic file with name nihms449166t8.jpg 9h, 82% -
10c 8i, graphic file with name nihms449166t9.jpg 9i, 89% -
11b 8j, graphic file with name nihms449166t10.jpg (R = CH2OH, R′ = Me) 9j, 77% 5:1
12 8k, graphic file with name nihms449166t11.jpg (R = CO2Et, R′ = Me) complex mixture
13 8l, graphic file with name nihms449166t12.jpg complex mixture
a

Conditions: [Rh(PPh3)3Cl] (0.5 mol %), alkyne 7 or 8 (1.1 equiv), CHCl3 (0.4 M), 50 °C, 24h unless noted otherwise. Isomeric ratios were determined by 1H NMR of crude products.

b

[Rh(PPh3)3Cl] (2 mol %)

c

[Rh(PPh3)3Cl] (10 mol %)