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. Author manuscript; available in PMC: 2008 Nov 21.
Published in final edited form as: J Am Chem Soc. 2005 Dec 7;127(48):17000–17006. doi: 10.1021/ja055608s

Table 2.

The coupling reaction of pyrrol– and indol–substituted aniline and terminal alkynes.a

entry amine alkyne product 4 (mol %) t (h) yd (%)b
graphic file with name nihms63206t22.jpg graphic file with name nihms63206t23.jpg graphic file with name nihms63206t24.jpg
1 R = Et 7a 1 24 96
2 R = Ph 7b 2 24 93
3 R = C6H4-p-OMe 7c 2 20 90
4 R = 2-SC4H3 7d 5 24 92
graphic file with name nihms63206t25.jpg graphic file with name nihms63206t26.jpg graphic file with name nihms63206t27.jpg
5 X = H R = Me 8a 2 20 93
6 X = H R = p-Tol 8b 3 24 75
7 X = H R = C6H4-p-Cl 8c 3 24 70
8 X = OMe R = Et 8d 3 24 82
graphic file with name nihms63206t28.jpg graphic file with name nihms63206t29.jpg graphic file with name nihms63206t30.jpg
9 R = n-Bu 9a 5 20 70
10 R = Ph 9b 5 24 91
a

Reaction conditions: amine (1.5 mmol), alkyne (2–5 mmol), Ru3(CO)12/HBF4·OEt2 (1:3), benzene (2–5 mL), 90–95 °C.

b

Isolated yield based on amine.