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. Author manuscript; available in PMC: 2012 Jul 4.
Published in final edited form as: Angew Chem Int Ed Engl. 2011 Jan 20;50(9):2171–2173. doi: 10.1002/anie.201007325

Table 1.

Cross-coupling of aryl sulfamates with morpholine.[a]

graphic file with name nihms383655t1.jpg
Entry Ar-OSO2NMe2 Product Yield
[%][b]
1 graphic file with name nihms383655t2.jpg graphic file with name nihms383655t3.jpg 95
2 graphic file with name nihms383655t4.jpg graphic file with name nihms383655t5.jpg 76
3 graphic file with name nihms383655t6.jpg graphic file with name nihms383655t7.jpg 77
4 graphic file with name nihms383655t8.jpg graphic file with name nihms383655t9.jpg 91
5[c] graphic file with name nihms383655t10.jpg graphic file with name nihms383655t11.jpg 80
6[d] graphic file with name nihms383655t12.jpg graphic file with name nihms383655t13.jpg 80
7[e] graphic file with name nihms383655t14.jpg graphic file with name nihms383655t15.jpg 50
8[f] graphic file with name nihms383655t16.jpg graphic file with name nihms383655t17.jpg 64
9[f] graphic file with name nihms383655t18.jpg graphic file with name nihms383655t19.jpg 74
10 graphic file with name nihms383655t20.jpg graphic file with name nihms383655t21.jpg 96
11 graphic file with name nihms383655t22.jpg graphic file with name nihms383655t23.jpg 86
12[d] graphic file with name nihms383655t24.jpg graphic file with name nihms383655t25.jpg 72
13 graphic file with name nihms383655t26.jpg graphic file with name nihms383655t27.jpg 86
[a]

Conditions unless otherwise stated: [Ni(cod)2] (5 mol%), 5 (10 mol%), sulfamate substrate (1 equiv), morpholine (1.2 equiv), NaOtBu (1.4 equiv), dioxane (0.2 m), 80°C for 3 h.

[b]

Yields of isolated product.

[c]

[Ni(cod)2] (10 mol%), 5 (20 mol%), NaOtBu (1.5 equiv).

[d]

[Ni-(cod)2] (15 mol%), 5 (30 mol%), morpholine (1.8 equiv), NaOtBu (2.2 equiv).

[e]

[Ni(cod)2] (20 mol%), 5 (40 mol%), NaOtBu (1.7 equiv), 60°C.

[f]

[Ni(cod)2] (15 mol%), 5 (30 mol%), NaOtBu (1.6 equiv).