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. 2019 Oct 2;9(54):31217–31223. doi: 10.1039/c9ra07604b

Iron-catalysed alkylations of allyl acetates (condition A).

graphic file with name c9ra07604b-u2.jpg
Entry Allyl acetate Product R′ Yielda [%]
1 graphic file with name c9ra07604b-u3.jpg graphic file with name c9ra07604b-u4.jpg H 85
2 Me 72
3 nC6H13 67
4 graphic file with name c9ra07604b-u5.jpg graphic file with name c9ra07604b-u6.jpg 61 (<5b)
5 graphic file with name c9ra07604b-u7.jpg 59
6 graphic file with name c9ra07604b-u8.jpg graphic file with name c9ra07604b-u9.jpg Me 80
7 Cl 0
8 Br 0
9 graphic file with name c9ra07604b-u10.jpg graphic file with name c9ra07604b-u11.jpg 37c
10 graphic file with name c9ra07604b-u12.jpg graphic file with name c9ra07604b-u13.jpg 53c
11 graphic file with name c9ra07604b-u14.jpg graphic file with name c9ra07604b-u15.jpg 16c
12 graphic file with name c9ra07604b-u16.jpg graphic file with name c9ra07604b-u17.jpg 64
a

Isolated yields; E/Z product ratios >50/1.

b

C9H19MgCl·LiCl was used.

c

10 mol% Fe(OAc)2, RMgBr addition over 1 h.