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. Author manuscript; available in PMC: 2017 Aug 4.
Published in final edited form as: Angew Chem Int Ed Engl. 2017 Mar 3;56(14):3951–3955. doi: 10.1002/anie.201612311

Table 2.

Scope of Aryl Halide

graphic file with name nihms882669u2.jpg
entry Ar–X product % yield 2 % yield 3
1a graphic file with name nihms882669t1.jpg
4 		graphic file with name nihms882669t2.jpg
2a 		70% 11%
1b 61% (1.2 gram scale) 14%
2 graphic file with name nihms882669t3.jpg
5 		graphic file with name nihms882669t4.jpg
2b 		47% (>95:5 meta/para) not observed
3 graphic file with name nihms882669t5.jpg
6 		graphic file with name nihms882669t6.jpg
2c 		26% (>95:5 meta/para) 26%
4 graphic file with name nihms882669t7.jpg
7 		graphic file with name nihms882669t8.jpg
2d 		42% (>95:5 meta/para) 21%
5 graphic file with name nihms882669t9.jpg
8 		graphic file with name nihms882669t10.jpg
2e 		44% (>95:5 meta/para) not observed
6 graphic file with name nihms882669t11.jpg
9 		graphic file with name nihms882669t12.jpg
2f 		44% (3.5:1 C5/C4 on benzofuran) not observed
7 graphic file with name nihms882669t13.jpg
10 		graphic file with name nihms882669t14.jpg
2g 		76% (>95:5 meta/para) 13%
8 graphic file with name nihms882669t15.jpg
11 		2g 68% (>95:5 meta/para) 14%
9 graphic file with name nihms882669t16.jpg
12 		2g 56% (1:1 meta/para) 14%
10 graphic file with name nihms882669t17.jpg
13 		graphic file with name nihms882669t18.jpg
2h 		52% (>95:5 meta/para) 13%
11 graphic file with name nihms882669t19.jpg
14 		2h 59% (3.5:1 meta/para) 15%
12 graphic file with name nihms882669t20.jpg
15 		2h 40% (1:1 meta/para) 13%

Conditions: 2 equiv indole, 1 equiv aryl halide, 4 equiv KOtBu, in DMSO at 80 °C for 35 h. Percentages represent isolated yields.