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. Author manuscript; available in PMC: 2008 Dec 1.
Published in final edited form as: J Org Chem. 2007 Apr 12;72(10):3896–3905. doi: 10.1021/jo070321u

Table 2.

Expanded Sulfonamide Substrate Scopea

entry substrate product(s)b temp; time yield (%)c
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8
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9
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10
120 °C; 24 h 49 exo (9)
46 endo (10)
2 graphic file with name nihms62275t4.jpg
11
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12
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13
160 °C; 72 h 23 CA (12)d
3 160 °C; 72 h 59 CA (12) + 21 HA (13)
4 graphic file with name nihms62275t7.jpg
14
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15
160 °C; 72 h 87d
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16
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17
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18
210 °C, 72 h 56 CA (17, trans : cis = 1 : 1), 16 HA (18, trans : cis = 1 : 1)
6 210 °C; μW, 3 h 52 CA (17, trans : cis = 1 : 1), 20 HA (18, trans : cis = 1 : 1)
7 graphic file with name nihms62275t12.jpg
19
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20
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21
180 °C, 72 h 65 CA (20, trans : cis = 3 : 1)
33 HA (21, trans : cis = 3 : 1)
8 graphic file with name nihms62275t15.jpg
22
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23
200 °C; 72 h 48
9 graphic file with name nihms62275t17.jpg
24
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25
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26
200 °C; 72 h 53 CA (25 only)
10 210 °C, μW, 3 h 55 CA (25) + 14 HA (26)
11 graphic file with name nihms62275t20.jpg
27
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28
200 °C; 72 h 43
a

Reaction conditions: 3 equiv Cu(ND)2, 1 equiv Cs2CO3, DMF (0.08–0.1 M), temp, time.

b

Selectivity determined by analysis of the crude 1H NMR spectrum, and by amount of the isolated adducts.

c

Yield refers to amount of product isolated by chromatography on silica gel.

d

Reaction run with Cu(OAc)2 instead of Cu(ND)2. CA = carboamination product, HA = hydroamination product, ND = neodecanoate.