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. Author manuscript; available in PMC: 2012 Mar 21.
Published in final edited form as: Chem Sci. 2011 Jun 10;2(9):1772–1776. doi: 10.1039/C1SC00194A

Table 2.

Substrate scopea,b

graphic file with name nihms355844u2.jpg
Entry R Ar Ar1 d.r. Yield [%]
1 4-ClPh Ph Ph >20 : 1 94 (4)
2 4-ClPh 4-BrPh Ph >20 : 1 87 (5)
3 4-ClPh 4-MePh Ph >20 : 1 61 (6)
4 4-ClPh 4-ClPh Ph >20 : 1 76 (7)
5 4-ClPh 2-Napth Ph >20 : 1 74 (8)
6 4-ClPh 2-ClPh Ph >20 : 1 75 (9)
7 4-ClPh 4-MeOPh Ph >20 : 1 71 (10)c
8 Ph 2-ClPh Ph >20 : 1 81 (11)c
9 Ph 4-MeOPh Ph >20 : 1 63 (12)c
10 Ph 4-MePh Ph >20 : 1 70 (13)c
11 Ph 2-Napth Ph >20 : 1 77 (14)c
12 4-MePh 4-ClPh Ph >20 : 1 75 (15)c
13 PhCH2 Ph Ph >20 : 1 86 (16)c
14 4-ClPh Ph 4-MePh >20 : 1 72 (17)d
15 4-ClPh Ph 4-BrPh >20 : 1 60 (18)d
16 Ph Ph 4-MePh >20 : 1 77 (19)d
a

General conditions: vinyl sulfone (1 equiv), nitrone (1.05 equiv), azolium salt A (20 mol%), NaOt-Bu (20 mol%), CH2Cl2 (0.10 M).

b

Yield of isolated products.

c

Vinyl sulfone (2 equiv), nitrone (1 equiv).

d

1,2-dichloroethane (0.10 M), 40 °C, no 4 Å MS.