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. Author manuscript; available in PMC: 2019 May 6.
Published in final edited form as: Synlett. 2017 Oct 12;29(2):181–184. doi: 10.1055/s-0036-1588578

Table 3.

Catalytic CuCN.2LiBr (5 mol%) Mediated Allylation of 1-Methyl- N,N-Dimethyl-4-pentene in THF with Representative Halides

graphic file with name nihms-1005099-t0015.jpg
Entry Halides Time Temp Productb Yielda,c
1 graphic file with name nihms-1005099-t0016.jpg 12 h 23 °C graphic file with name nihms-1005099-t0017.jpg ≥ 95%
2 graphic file with name nihms-1005099-t0018.jpg 10h 23 °C graphic file with name nihms-1005099-t0019.jpg ≥ 95%
3 graphic file with name nihms-1005099-t0020.jpg 5 h 23 °C graphic file with name nihms-1005099-t0021.jpg 60%
4 graphic file with name nihms-1005099-t0022.jpg 4 h 23 °C graphic file with name nihms-1005099-t0023.jpg 65%
a

Monitored by No-D 1H NMR using disappearance of C-Zn methylene peak to determine completion.7

b

Products were isolated as TFA salts subsequent to allylation in THF.

c

A small quantity of the TFA salt of the starting N,N-dimethylhydrazinoalkene 1 was admixed with the product.