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. Author manuscript; available in PMC: 2013 Jan 25.
Published in final edited form as: J Am Chem Soc. 2012 Jan 3;134(3):1490–1493. doi: 10.1021/ja211269w

Table 3.

NHC–Cu-Catalyzed Allenyl Additions to Aryl-Containing Disubstituted Allylic Phosphatesa

graphic file with name nihms-347402-t0010.jpg

entry Ar conv (%);b
yield (%)c 		SN2′:SN2b erd
1 Ph; 5a >98; 79 96:4 95.5:4.5
2 o-FC6H4, 5b >98; 79 94:6 96:4
3 o-BrC6H4, 5c >98; 80 88:12 96:4
4 o-CF3C6H4, 5d >98; 67 77:23 96:4
5 o-MeC6H4, 5e >98; 68 >98:2 95:5
6 o-MeOC6H4, 5f >98; 79 >98:2 96.5:3.5
7 m-BrC6H4, 5g >98; 92 97:3 98.5:1.5
8 m-CF3C6H4, 5h >98; 65 91:9 98:2
9 m-MeC6H4, 5i >98; 71 >98:2 97:3
10 2-naphthyl, 5j >98; 88 98:2 99:1
11 p-ClC6H4, 5k >98; 64 93:7 96:4
12 p-O2NC6H4, 5l >98; 69 85:15 97 :3
a

Reactions performed under N2 atm.

b

Determined by analysis of 400 MHz 1H NMR spectra of unpurified mixtures; conversion refers to consumption of the substrate.

c

Yields of isolated and purified allenyl addition products.

d

Determined by GLC analysis; see the Supporting Information for details.