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. Author manuscript; available in PMC: 2013 Oct 10.
Published in final edited form as: J Am Chem Soc. 2012 Sep 24;134(40):16449–16451. doi: 10.1021/ja305448w

Table 1.

Amination of OctylB(pin).a

graphic file with name nihms410230u1.jpg
entry CH3ONH2 (equiv) base (equiv) yield (%)
1 1.0 n-BuLi (1.0) 41
2 2.0 n-BuLi (2.0) 72
3 3.0 n-BuLi (3.0) 84
4 3.0 MeLi (3.0) 48
5 3.0 NaH (3.0) <5
6 3.0 KH (3.0) <5
7 3.0 K(OtBu) (3.0) 16
8 3.0 Li(OtBu) (3.0) <5
a

Reactions were conducted as described in the text. The percent value given refers to the isolated yield of purified material and is an average of two experiments.