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. 2014 Jun 11;16(12):3412–3415. doi: 10.1021/ol5015976

Table 2. Scope of Pd-Catalyzed Carboaminationa.

graphic file with name ol-2014-015976_0009.jpg

entry R1 R product yield (%)b drc (crude)
1 H Ph 10a 89 7:1
2 H p-tBu-C6H4 10b 78 6:1
3 H p-MeO-C6H4 10c 70 7:1
4 H p-benzophenone 10d 61d 8:1 (5:1)
5 H o-Me-C6H4 10e 87 5:1
6 H 1-cyclohexenyl 10f 63d 6:1
7 H 1-decenyl 10g 45d 10:1f,g
8 allyl Ph 10h 65e 20:1 (12:1)
9 allyl p-MeO-C6H4 10i 63e >20:1 (13:1)
a

Reaction conditions: 1.0 equiv 9a or 9b, 2.0 equiv R-OTf, 2.0 equiv LiOtBu, 4 mol % Pd(OAc)2, 10 mol % C-Phos, tBuOH (0.1 M), 82 °C, 16 h.

b

Isolated yield (average of two or more runs).

c

Diastereomeric ratio of the pure isolated material. Diastereomeric ratios of isolated materials were identical to those of the crude products unless otherwise noted.

d

The reaction was conducted with 3.0 equiv LiOtBu and 3.0 equiv R-OTf.

e

The reaction time was 2 h.

f

1-Decenyl triflate was employed as 5:1 mixture of E:Z isomers.

g

The dr was determined following hydrogenation of 10g. The crude dr of 10g could not be determined directly due to the mixture of diastereomers and E:Z isomer products. However, we estimate the crude dr to be ca. 5–10:1.