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. Author manuscript; available in PMC: 2013 Sep 21.
Published in final edited form as: J Org Chem. 2012 Sep 6;77(18):8257–8267. doi: 10.1021/jo3015825

Table 3.

One-Pot Phosphine-Catalyzed Syntheses of 3-Substituted Quinolinesa

graphic file with name nihms404426t17.jpg

entry substrate product time
(min)
yield
(%)b
1 graphic file with name nihms404426t18.jpg graphic file with name nihms404426t19.jpg 240 88
2 graphic file with name nihms404426t20.jpg graphic file with name nihms404426t21.jpg 30 95
3 graphic file with name nihms404426t22.jpg graphic file with name nihms404426t23.jpg 20 99
4 graphic file with name nihms404426t24.jpg graphic file with name nihms404426t25.jpg 5 98
5 graphic file with name nihms404426t26.jpg graphic file with name nihms404426t27.jpg 5 98
6 graphic file with name nihms404426t28.jpg graphic file with name nihms404426t29.jpg 5 97
7 graphic file with name nihms404426t30.jpg graphic file with name nihms404426t31.jpg 5 96

8 graphic file with name nihms404426t32.jpg graphic file with name nihms404426t33.jpg 5 98
9 graphic file with name nihms404426t34.jpg graphic file with name nihms404426t35.jpg 90 93
10 graphic file with name nihms404426t36.jpg graphic file with name nihms404426t37.jpg 40 86
11c graphic file with name nihms404426t38.jpg graphic file with name nihms404426t39.jpg 5 63
12 graphic file with name nihms404426t40.jpg graphic file with name nihms404426t41.jpg 600 61
13 graphic file with name nihms404426t42.jpg graphic file with name nihms404426t43.jpg 5 30
a

2 (1.5 equiv.) was added in one portion to a solution of 1a (0.2 M) and PPh3 (10 mol%) in MeCN.

b

Isolated yield.

c

Diacetylene 2q (0.10 mmol) was added to a solution of 1a (0.21 mmol, 0.21 M) and PPh3 (20 mol%) in MeCN.