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. Author manuscript; available in PMC: 2015 Jan 1.
Published in final edited form as: Top Curr Chem. 2014;343:1–32. doi: 10.1007/128_2013_481

Table 7.

Varying the radical precursors and acceptors in Cu(II) catalyzed addition to N-acylhydrazones.

graphic file with name nihms602654u7.jpg
entry halide hydrazone catalyst load % yieldb % eec
1 iPrI 60a 1 equiv 66 95
2 i-PrI 60b 1 equiv 46 90
3 i-PrI 60c 1 equiv 53 81
4 EtId 60a 1 equiv 88 83
5 c-C5H9Id 1 equiv 86 84
6 c-C6H11Id 1 equiv 84 89
7 ClCH2Id 1 equiv 44e 95
8 iPrI 0.5 equiv 71 81
9 iPrI 0.2 equiv 83 58
10 iPrI 0.1 equiv 74 46
a

Reaction conditions: see Table 6.

b

Isolated yield, %.

c

Enantiomeric excess, % (hexane:2-propanol, Chiralcel OD or AD).

d

10 equiv of alkyl halide was used.

e

56% recovery of unreacted hydrazone.