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. Author manuscript; available in PMC: 2010 Aug 26.
Published in final edited form as: J Am Chem Soc. 2009 Aug 26;131(33):11701–11706. doi: 10.1021/ja903939k

Table 1.

Exogenous, Catalytic Brønsted Base Additives for Direct Allylic C—H Amination

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entry additive yield(%)a L:Bb E:Zc
1 none 1d - -
2 (S,S)-Cr(salen)Cl 2 50 11:1 19:1
3 pyridine 9 12:1 14:1
4 2,6-di-tert-butylpyridine - - -
5 N-isopropylamine - - -
6 N,N-diisopropylamine 66 12:1 15:1
7 triethylamine 60 14:1 15:1
8 N,N-diisopropylethylamine 66 11:1 17:1
9 MeOC(O)NTsH-DIPEAe 9 6:1 10:1
a

isolated yield of linear product.

b

linear/branched ratio determined by HPLC of crude reaction mixture.

c

determined by 1H NMR after chromatography.

d

1H NMR yield by comparison with internal standard.

e

2.0 equiv. of the pre-formed salt was used instead of MeOC(O)NHTs.