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. 2014 Jan 28;136(5):2149–2161. doi: 10.1021/ja4126565

Table 1. Initial Screening of Different NHC–Cu Complexesa.

1.

entry imidazolinium salt conv (%)b yield (%)c SN2′:SN2b erd
1 4 38 31 67:33 45:55
2 5 76 59 79:21 74:26
3 6 38 30 >98:2 78:22
4 7 91 90 >98:2 41:59
5 8 72 70 98:2 34:66
6 9a 98 93 98:2 87:13
7 9b 97 97 98:2 92:8
a

Reactions performed under N2 atm.

b

Conversion (allylic phosphate consumption) and site selectivity (±2%) were determined by analysis of 400 MHz 1H NMR spectra of product mixtures prior to purification.

c

Yield of products (±5%) after purification by silica gel chromatography.

d

Enantioselectivity (±2%) determined by HPLC analysis. See the Supporting Information for experimental and analytical details.