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. Author manuscript; available in PMC: 2014 Sep 16.
Published in final edited form as: Chemistry. 2013 Jul 22;19(38):12771–12777. doi: 10.1002/chem.201301800

Table 3.

Synthesis of indoles and larger ring enamides.[a]

Entry Substrate Product Yield
[%][b]
graphic file with name nihms-583677-t0023.jpg graphic file with name nihms-583677-t0024.jpg
1 12a, R1, R2 = H, R3 = Ts 13 a, R1, R2 = H, R3 = Ts 66
2[c] 12b, R1 = Me, R2 = H,
R3 = Ts
13 b, R1 = Me, R2 = H,
R3 = Ts
90
3[c] 12 c, R1 = Ph, R2 = H,
R3 = Ts
13 c, R1 = Ph, R2 = H,
R3 = Ts
97
4[d] 12 c 13 c 70
5 12d, R1 = H, R2 = Ph,
R3 = Ts
13 d, R1 = H, R2 = Ph,
R3 = Ts
41
6[c] graphic file with name nihms-583677-t0025.jpg graphic file with name nihms-583677-t0026.jpg 95
7[c] graphic file with name nihms-583677-t0027.jpg graphic file with name nihms-583677-t0028.jpg 82
8 16 17 (unsaturated)/ 94
18 (saturated) (5:1)
9[e] graphic file with name nihms-583677-t0029.jpg 17 (exclusively) 90
10 19 n.r.
[a]

Same conditions as in Table 1 for entry 5 were used, except no external alkene 2 was added.

[b]

Isolated yield.

[c]

Reaction run with 5 mol % Cu(OTf)2·7.

[d]

Reaction run in the absence of copper.

[e]

Reaction run in CF3Ph instead of CH3Ph.