Skip to main content
. Author manuscript; available in PMC: 2015 Jul 7.
Published in final edited form as: Chemistry. 2014 Jun 17;20(28):8782–8790. doi: 10.1002/chem.201402258

Table 2.

Pd-Catalyzed Carboamination of N-Allyl Sulfamides [a]

graphic file with name nihms604343t2.jpg
Entry R R1 R2 Product Yield (%)[b]
1 Bn Bn p-Me-C6H4 2c 85
2 Bn Bn p-NC-C6H4 2a 90
3 Bn Bn p-MeO-C6H4 2d 90
4 Bn Bn o-Me-C6H4 2e 85
5 Bn Bn 1-cyclohexenyl 2f 87[c]
6 Bn Bn E-1-decenyl[e] 2g 80[d,e,f]
7 Me Bn p-Cl-C6H4 2h 79
8 Bn PMB p-Me-C6H4 2i 90
9 Bn Me m-F3C-C6H4 2j 86
10 Bn tBu p-MeO-C6H4 2k 92
11 Bn PMP Ph 2l 90[g]
12 Me Bn graphic file with name nihms604343t3.jpg 2m 84
13 tBu Bn m-F3C-C6H4 2n 88[h]
14 H allyl Ph 2o 51[i]
[a]

Reaction Conditions: 1.0 equiv 1, 1.2 equiv R2OTf, 1.4 equiv LiOtBu, 2 mol % Pd(OAc)2, 5 mol % RuPhos, PhCF3 (0.25 M), 100 °C.

[b]

Isolated yield (average of two experiments).

[c]

The reaction was conducted using Brettphos as ligand.

[d]

The reaction was conducted using tBu-Davephos as ligand.

[e]

The alkenyl triflate was used as a 5:1 mixture of E:Z isomers, and the product was obtained as a 5:1 E:Z mixture.

[f]

The reaction was conducted using 1.4 equiv R2OTf and 1.6 equiv LiOtBu.

[g]

The reaction was conducted using tBu-X-Phos as ligand.

[h]

The reaction was conducted using 7.5 mol % ligand.

[i]

The reaction was conducted using 2.4 equiv R2OTf and 2.4 equiv LiOtBu.