FULL PAPERS
Ji-zong Zhang and Yu Tang
7.83 (m, 2H), 7.79–7.75 (m, 2H), 7.19 (t, J=8.6 Hz, 2H),
5.38 (s, 2H); 19F NMR (376 MHz, CDCl3): d=À102.9–103.0
(m, 1F); 13C NMR (150 MHz, CDCl3): d=78.7, 116.1 (d, J=
21.9 Hz), 123.8, 128.8, 131.3, 131.4, 134.8, 163.0, 166.3 (d, J=
254.9 Hz) 190.9; MS (ESI): m/e (% relative intensity)=
322.0 (100) (M+Na)+; HR-MS: m/e=300.0667, calcd. for
C16H10FNO4 (M+H)+: 300.0672.
130.5, 131.7, 134.0, 134.2, 134.7, 163.1, 195.4; MS (ESI):
m/e (% relative intensity)=332.2 (100) (M+H)+; HR-MS:
m/e=354.0738, calcd. for C20H13NO4 (M+Na)+: 354.0742.
2-(2-Oxo-1,2-diphenylethoxy)isoindoline-1,3-dione (5a):
Following the general procedure using trans-stilbene or cis-
stilbene in place of styrene: white solid; yield: 72 mg (65%)
and 67 mg (65%), respectively; mp 162–1648C; Rf =0.54
(30% EtOAc/petroleum ether); 1H NMR (600 MHz,
CDCl3): d=8.01 (d, J=7.9 Hz, 2H), 7.77–7.75 (m, 2H),
7.71–7.68 (m, 2H), 7.63–7.61 (m, 2H), 7.52 (t, J=7.3 Hz,
1H), 7.41 (t, J=7.6 Hz, 2H), 7.36–7.35 (m, 3H), 6.77 (s,
1H); 13C NMR (150 MHz, CDCl3): d=88.3, 123.6, 128.67,
128.72, 129.0, 129.1, 129.5, 130.1, 132.6, 133.7, 134.5, 134.7,
163.2, 192.8; MS (ESI): m/e (% relative intensity)=357.9
(100) (M+H)+; HR-MS: m/e=358.1079, calcd. for
C22H15NO4 (M+H)+: 358.1079.
2-[(3-Hydroxy-1-oxo-1-phenylpropan-2-yl)oxy]isoindo-
line-1,3-dione (5d): Following the general procedure using
cinnamyl alcohol in place of styrene: colorless oil; yield:
44 mg (45%); Rf =0.21 (30% EtOAc/petroleum ether);
1H NMR (400 MHz, CDCl3): d=8.08 (d, J=7.2 Hz, 2H),
7.86–7.82 (m, 2H), 7.80–7.76 (m, 2H), 7.61 (t, J=7.3 Hz,
1H), 7.50 (t, J=7.8 Hz, 2H), 5.53 (q, J=4.2 Hz, 1H), 4.19–
4.13 (m, 1H), 4.05–4.01 (m, 1H); 13C NMR (100 MHz,
CDCl3): d=60.8, 88.5, 124.0, 128.6, 128.8, 129.0, 133.9, 135.0,
135.1, 164.3, 193.8; MS (ESI): m/e (% relative intensity)=
312.1 (100) (M+H)+; m/e=312.0872, calcd. for C17H13NO5
(M+H)+: 312.0872.
2-[(1-Oxo-1-phenylpropan-2-yl)oxy]isoindoline-1,3-dione
(5e): Following the general procedure using (Z/E)-b-methyl-
styrene in place of styrene: colorless oil; yield: 63 mg
(69%); Rf =0.54 (30% EtOAc/petroleum ether); 1H NMR
(400 MHz, CDCl3): d=8.16 (d, J=7.3 Hz, 2H), 7.84–7.80
(m, 2H), 7.77–7.73 (m, 2H), 7.60 (t, J=7.4 Hz, 1H), 7.50 (t,
J=7.8 Hz, 2H), 5.75 (q, J=6.7 Hz, 1H), 1.69 (d, J=6.7 Hz,
3H); 13C NMR (100 MHz, CDCl3): d=16.2, 83.6, 123.7,
128.7, 128.8, 129.2, 133.8, 134.68, 134.73, 163.7, 195.3; MS
(ESI): m/e (% relative intensity)=296.1 (100) (M+H)+;
HR-MS: m/e=296.0923, calcd. for C17H13NO4 (M+H)+:
296.0923.
2-[(1-Oxo-1-phenylhept-6-en-2-yl)oxy]isoindoline-1,3-
dione (5f): Following the general procedure using hepta-1,6-
dien-1-ylbenzene in place of styrene: colorless oil; yield:
57 mg (53%); Rf =0.60 (30% EtOAc/petroleum ether);
1H NMR (400 MHz, CDCl3): d=8.07 (d, J=7.7 Hz, 2H),
7.82–7.77 (m, 2H), 7.75–7.71 (m, 2H), 7.59 (t, J=7.2 Hz,
1H), 7.48 (t, J=7.7 Hz, 2H), 5.83–5.73 (m, 1H), 5.60 (t, J=
6.0 Hz, 1H), 5.04–4.94 (m, 2H), 2.16 (q, J=7.0 Hz, 2H),
2.07 (p, J=7.8 Hz, 2H), 1.73 (p, J=7.6 Hz, 2H); 13C NMR
(100 MHz, CDCl3): d=24.3, 30.8, 33.2, 88.1, 115.3, 123.6,
128.7, 128.8, 129.0, 133.8, 134.6, 134.9, 137.9, 163.4, 195.9;
MS (ESI): m/e (% relative intensity)=350.1 (100) (M+H)+;
HR-MS: m/e=372.1213, calcd. for C21H19NO4 (M+Na)+:
372.1212.
2-[2-(4-Methoxyphenyl)-2-oxoethoxy]isoindoline-1,3-
dione (3h): Following the general procedure using 4-me-
thoxystyrene in place of styrene: white solid; yield: 64 mg
(66%); mp 133–1358C; Rf =0.33 (30% EtOAc/petroleum
1
ether); H NMR (600 MHz, CDCl3): d=8.01 (d, J=8.8 Hz,
2H), 7.86–7.83 (m, 2H), 7.78–7.75 (m, 2H), 6.97 (d, J=
8.8 Hz, 2H), 5.39 (s, 2H), 3.88 (s, 3H); 13C NMR (150 MHz,
CDCl3): d=55.6, 78.5, 114.1, 123.7, 127.5, 128.8, 130.8, 134.7,
163.0, 164.2, 190.7; MS (ESI): m/e (% relative intensity)=
312.2 (100) (M+H)+; HR-MS: m/e=312.0875, calcd. for
C17H13NO5 (M+H)+: 312.0872.
2-{2-[4-(tert-Butyl)phenyl]-2-oxoethoxy}isoindoline-1,3-
dione (3i): Following the general procedure using 4-tert-bu-
tylstyrene in place of styrene: white solid; yield: 75 mg
(72%); mp 162–1648C; Rf =0.55 (30% EtOAc/petroleum
1
ether); H NMR (600 MHz, CDCl3): d=7.95 (d, J=7.8 Hz,
2H), 7.89–7.82 (m, 2H), 7.79–7.73 (m, 2H), 7.51 (d, J=
7.8 Hz, 2H), 5.44 (s, 2H), 1.34 (s, 9H); 13C NMR (150 MHz,
CDCl3): d=31.0, 35.3, 78.4, 123.7, 125.8, 128.3, 128.8, 131.9,
134.7, 158.0, 163.0, 191.8; MS (ESI): m/e (% relative intensi-
ty)=338.4 (100) (M+H)+; HR-MS: m/e=360.1207, calcd
for C20H19NO4 (M+Na)+: 360.1212.
2-[2-([1,1’-Biphenyl]-4-yl)-2-oxoethoxy]isoindoline-1,3-di-
one (3j): Following the general procedure using 4-vinylbi-
phenyl in place of styrene: white solid; yield: 65 mg (59%);
mp 168–1718C; Rf =0.36 (30% EtOAc/petroleum ether);
1H NMR (600 MHz, CDCl3): d=8.09 (d, J=8.4 Hz, 2H),
7.87–7.86 (m, 2H), 7.78–7.75 (m, 2H), 7.73 (d, J=8.4 Hz,
2H), 7.63 (d, J=7.3 Hz, 2H), 7.48 (t, J=7.4 Hz, 2H), 7.41
(t, J=7.3 Hz, 1H), 5.49 (s,2H); 13C NMR (150 MHz,
CDCl3): d=78.6, 123.8, 127.3, 127.5, 128.5, 128.8, 128.97,
129.03, 133.1, 134.7, 139.6, 146.8, 163.1, 191.9; MS (ESI):
m/e (% relative intensity)=358.2 (100) (M+H)+; HR-MS:
m/e=358.1072, calcd. for C22H15NO4 (M+H)+: 358.1079.
2-{2-Oxo-2-[4-(trifluoromethyl)phenyl]ethoxy}isoindoline-
1,3-dione (3k): Following the general procedure using 4-(tri-
fluoromethyl)styrene in place of styrene: white solid; yield:
91 mg (84%); mp 149–1528C; Rf =0.46 (30% EtOAc/petro-
leum ether); 1H NMR (600 MHz, CDCl3): d=8.18 (d, J=
8.1 Hz, 2H), 7.88–7.84 (m, 2H), 7.80–7.76 (m, 4H), 5.41 (s,
2H); 19F NMR (564 MHz, CDCl3): d=À63.3 (s, 3F);
13C NMR (150 MHz, CDCl3): d=78.9, 123.4 (d, J=
271.2 Hz), 123.8, 125.9 (q, J=3.4 Hz), 128.7, 129.0, 134.8,
135.2 (q, J=32.8 Hz), 137.1, 163.0, 191.7; MS (ESI): m/e (%
relative intensity)=349.9 (100) (M+H)+; HR-MS: m/e=
350.0639, calcd. for C17H10F3NO4 (M+H)+: 350.0640.
2-[2-(Naphthalen-1-yl)-2-oxoethoxy]isoindoline-1,3-dione
(3n): Following the general procedure using 1-vinylnaphtha-
lene in place of styrene: white solid,; yield: 58 mg (56%);
mp 161–1648C; Rf =0.40 (30% EtOAc/petroleum ether);
1H NMR (600 MHz, CDCl3): d=8.78 (d, J=8.6 Hz, 1H),
8.05 (t, J=8.0 Hz, 2H), 7.88 (d, J=8.1 Hz, 1H), 7.85–7.81
(m, 2H), 7.76–7.72 (m, 2H), 7.62 (t, J=7.7 Hz, 1H), 7.57–
7.52 (m, 2H), 5.48 (s, 2H); 13C NMR (150 MHz, CDCl3):
d=79.5, 123.7, 124.3, 125.7, 126.8, 128.5, 128.6, 128.8, 129.3,
(Z)-2-[(1-Oxo-1-phenyloct-5-en-2-yl)oxy]isoindoline-1,3-
dione (5g): Following the general procedure using (5Z)-
octa-1,5-dien-1-ylbenzene in place of styrene: colorless oil;
yield: 36 mg (32%); Rf =0.65 (30% EtOAc/petroleum
1
ether); H NMR (400 MHz, CDCl3): d=8.08 (d, J=7.9 Hz,
2H), 7.81–7.78 (m, 2H), 7.74–7.71 (m, 2H), 7.59 (t, J=
7.3 Hz, 1H), 7.48 (t, J=7.8 Hz, 2H), 5.62 (t, J=5.8 Hz, 1H),
5.47–5.33 (m, 2H), 2.43–2.28 (m, 2H), 2.18–1.98 (m, 4H),
760
ꢁ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2016, 358, 752 – 764