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. Author manuscript; available in PMC: 2006 Sep 25.
Published in final edited form as: J Am Chem Soc. 2003 Oct 1;125(39):11956–11963. doi: 10.1021/ja0361547

Table 3.

Hydroamination of Aryl-Substituted Aminoallenes (5 Mol % of Catalyst in C6D6, 75°C)

isolated yielda
entry substrate major product cat. t / h imine allyamine
1 graphic file with name nihms4154t4.jpg graphic file with name nihms4154t5.jpg 3 22 (95) (5)
2 13 1 84 ---
3 graphic file with name nihms4154t6.jpg graphic file with name nihms4154t7.jpg 3 9 (90) (10)
4 13 5 79 ---
5 graphic file with name nihms4154t8.jpg graphic file with name nihms4154t9.jpg 3 4 (92) (8)
6 13 1.5 95 ---
7 graphic file with name nihms4154t10.jpg graphic file with name nihms4154t11.jpg 13 10 93 ---
8 graphic file with name nihms4154t12.jpg graphic file with name nihms4154t13.jpg 13 2 88 ---
9 graphic file with name nihms4154t14.jpg graphic file with name nihms4154t15.jpg 13b 3 (93) (7)
10 graphic file with name nihms4154t16.jpg --- 13b 24 --- ---
a

Yields in parentheses refer to ratio of imine/allylamine by NMR after complete and selective conversion of the starting material (versus internal standard)

b

10 mol %.