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Multimetallic Iridium-Tin (Ir-Sn3) Catalyst in N-Acyliminium Ion Chemistry
(d, J=15.6 Hz, 1H), 4.79 (d, J=4.4 Hz, 1H), 4.83 (d, J=
4.0 Hz, 1H), 5.29–5.33 (m, 2H), 5.42 (d, J=4.8 Hz, 1H),
7.24–7.60 (m, 32H), 7.72 (d, J=8.4 Hz, 2H), 7.77 (d, J=
8.8 Hz, 2H), 7.84 (d, J=8.0 Hz, 1H), 7.90 (d, J=8.0 Hz,
1H); 13C NMR (100 MHz, CDCl3): d=13.4, 13.7, 44.5, 45.0,
55.3, 56.9, 57.9, 58.1, 61.5, 62.0, 123.3, 123.5, 124.5, 127.1,
127.4, 127.6, 127.9, 128.0, 128.21, 128.24, 128.4, 128.52,
128.58, 128.63, 128.68, 128.71, 128.78, 128.8, 131.3, 131.7,
133.7, 133.8, 135.5, 136.1, 136.4, 137.0, 142.5, 143.5, 166.4,
167.4, 168.6, 169.1, 192.9; HR-MS (ESI): m/z=414.1678,
calcd. for C26H24NO4 [M+H]+: 414.1705.
118.2, 123.5, 123.7, 130.1, 132.1, 132.3, 132.5, 139.9, 167.1;
HR-MS (ESI): m/z=228.0995, calcd. for C14H14NO2 [M+
H]+: 228.1025.
3-(4-Methoxyphenylthio)-2-phenethylisoindolin-1-one
(9l): White solid; yield: 92 mg (98%); mp 96–988C;
1H NMR (200 MHz, CDCl3): d=2.98 (t, J=7.4 Hz, 2H),
3.68 (s, 3H), 3.72–3.87 (m, 1H), 4.25–4.39 (m, 1H), 5.28 (s,
1H), 6.55 (d, J=8.8 Hz, 2H), 6.88 (d, J=8.8 Hz, 2H), 7.19–
7.58 (m, 9H); 13C NMR (54.6 MHz, CDCl3): d=34.6, 41.1,
55.1, 67.1, 114.1, 118.0, 123.0, 123.6, 126.5, 128.5, 128.6,
128.8, 131.4, 131.7, 137.1, 138.7, 143.0, 160.4, 167.4; HR-MS
(ESI): m/z=376.1367, calcd. for C23H22NO2S [M+H]+:
376.1371.
N-(2-Allyl-3-oxoisoindolin-1-yl)benzenesulfonamide (9b):
1
White solid; yield: 75 mg (92%); mp 184–1868C; H NMR
(200 MHz, CDCl3): d=3.62 (dd, J=6.4 and 15.8 Hz, 1H),
4.19 (dd, J=4.4 and 15.6 Hz, 1H), 4.96–5.13 (m, 2H), 5.54
(d, J=10.0 Hz, 1H), 5.59–5.75 (m, 1H), 5.80 (d, J=10.0 Hz,
1H), 6.91–6.95 (m, 1H), 7.41–7.76 (m, 6H), 8.01 (d, J=
7.0 Hz, 2H); 13C NMR (100 MHz, CDCl3): d=41.1, 67.4,
117.7, 123.0, 123.4, 126.8, 129.3, 129.7, 130.9, 131.8, 132.4,
133.0, 141.5, 142.1, 167.0; HR-MS (ESI): m/z=329.0931,
calcd. for C17H17N2O3S [M+H]+: 329.0960.
N-(2-Benzyl-3-oxoisoindolin-1-yl)benzamide (9c): White
solid; yield: 73 mg (86%); mp 188–1908C; 1H NMR
(200 MHz, CDCl3): d=4.41 (d, J=14.8 Hz, 1H), 4.68 (d, J=
14.6 Hz, 1H), 6.79 (d, J=9.4 Hz, 1H), 7.24–7.67 (m, 13H),
7.90 (d, J=7.0 Hz, 2H); 13C NMR (100 MHz, CDCl3): d=
43.6, 63.9, 123.2, 123.3, 127.5, 127.6, 128.5, 128.6, 129.3,
131.4, 132.2, 132.3, 132.9, 136.8, 143.1, 167.8; HR-MS (ESI):
m/z=343.1459, calcd. for C22H19N2O2 [M+H]+: 343.1447.
N-(2-Benzyl-3-oxoisoindolin-1-yl)acetamide (9d): White
solid; yield: 58 mg (83%); mp 208–2108C; 1H NMR
(200 MHz, CDCl3): d=1.94 (s, 3H), 4.52 (d, J=14.8 Hz,
1H), 4.66 (d, J=14.8 Hz, 1H), 5.97 (d, J=10.0 Hz, 1H),
6.53 (d, J=10.0 Hz, 1H), 7.20–7.60 (m, 8H), 7.73 (d, J=
6.8 Hz, 1H); 13C NMR (100 MHz, CDCl3): d=23.3, 44.0,
63.8, 123.3, 123.5, 127.8, 128.6, 128.8, 129.7, 131.8, 132.5,
137.3, 142.9, 167.8, 171.2; HR-MS (ESI): m/z=303.1103,
calcd. for C17H16N2O2Na [M+Na]+: 303.1109.
2-Allyl-3-(3-phenylpropoxy)isoindolin-1-one (9g): Colour-
less oil; yield: 70 mg (91%); 1H NMR (200 MHz, CDCl3):
d=1.77–1.94 (m, 2H), 2.61–2.69 (m, 2H), 2.94–3.05 (m,
1H), 3.15–3.26 (m, 1H), 3.75 (dd, J=7.0 and 15.2 Hz, 1H),
4.51 (dd, J=4.8 and 15.4 Hz, 1H), 5.20–5.30 (m, 2H), 5.78–
5.97 (m, 1H), 5.89 (s, 1H), 7.13–7.31 (m, 5H), 7.50–7.58 (m,
3H), 7.82–7.86 (m, 1H); 13C NMR (54.6 MHz, CDCl3): d=
31.1, 32.2, 41.9, 61.6, 85.5, 117.9, 123.3, 123.4, 125.8, 128.2,
128.3, 129.8, 131.9, 132.4, 132.6, 141.4, 167.2; HR-MS (ESI):
m/z=308.1607, calcd. for C20H22NO2 [M +H]+: 308.1651.
2-Benzyl-3-(prop-2-ynyloxy)isoindolin-1-one (9h): Colour-
less oil; yield: 64 mg (92%); 1H NMR (200 MHz, CDCl3):
d=2.42 (t, J=2.4 Hz, 1H), 3.75 (d, J=2.4 Hz, 2H), 4.31 (d,
J=14.8 Hz, 1H), 5.18 (d, J=14.8 Hz, 1H), 5.78 (s, 1H),
7.23–7.59 (m, 8H), 7.84–7.89 (m, 1H); 13C NMR (54.6 MHz,
CDCl3): d=43.4, 51.0, 74.6, 79.0, 85.3, 123.7, 127.6, 128.5,
128.6, 130.2, 132.2, 132.5, 136.6, 139.8, 167.2; HR-MS (ESI):
m/z=278.1132, calcd. for C18H16NO2 [M+H]+: 278.1181.
2-Allyl-3-(prop-2-ynyloxy)isoindolin-1-one (9i): Colourless
oil; yield: 51 mg (90%); 1H NMR (200 MHz, CDCl3): d=
2.42 (t, J=2.4 Hz, 1H), 3.78–3.90 (m, 3H), 4.46 (dd, J=4.8
and 15.2 Hz, 1H), 5.18–5.31 (m, 2H), 5.76–5.91 (m, 1H),
5.93 (s, 1H), 7.48–7.59 (m, 3H), 7.80–7.85 (m, 1H);
13C NMR (54.6 MHz, CDCl3): d=42.1, 51.0, 74.5, 79.0, 85.4,
2-Benzyl-3-(2-hydroxyethylthio)isoindolin-1-one
(9m):
Yellow oil; yield: 67 mg (89%); 1H NMR (400 MHz,
CDCl3): d= 2.07–2.20 (m, 2H), 3.28–3.34 (m, 1H), 3.37–
3.43 (m, 1H), 4.39 (d, J=14.8 Hz, 1H), 5.32 (s, 1H), 5.36 (d,
J=14.8 Hz, 1H), 7.26–7.35 (m, 5H), 7.48–7.52 (m, 1H),
7.56–7.61 (m, 2H), 7.88 (d, J=7.2 Hz, 1H); 13C NMR
(100 MHz, CDCl3): d=29.2, 42.8, 61.0, 62.4, 123.5, 123.6,
127.7, 128.5, 128.7, 129.0, 131.6, 132.3, 136.5, 143.4, 167.4;
HR-MS (ESI): m/z=300.1047, calcd. for C17H18NO2S [M +
H]+: 300.1058.
2-Allyl-3-(2-hydroxyethylthio)isoindolin-1-one
(9n):
Yellow oil; yield: 57 mg (92%); 1H NMR (200 MHz,
CDCl3): d=2.02–2.24 (m, 2H), 3.24–3.46 (m, 2H), 3.92 (dd,
J=7.6 and 15.4 Hz, 1H), 4.70 (dd, J=4.4 and 15.4 Hz, 1H),
5.21–5.30 (m, 2H), 5.54 (s, 1H), 5.73–5.93 (m, 1H), 7.46–
7.66 (m, 3H), 7.84 (d, J=7.4 Hz, 1H); 13C NMR (100 MHz,
CDCl3): d=29.1, 41.6, 60.9, 62.7, 118.4, 123.4, 123.5, 129.0,
131.6, 132.2, 143.4, 167.3; HR-MS (ESI): m/z=250.0908,
calcd. for C13H16NO2S [M+H]+: 250.0902.
1-Benzyl-5-(4-methoxyphenylthio)pyrrolidin-2-one (9p):
Yellow solid; yield: 73 mg (93%); mp 95–978C; 1H NMR
(400 MHz, CDCl3): d=1.60–1.69 (m, 1H), 2.10–2.43 (m,
3H), 3.83 (s, 3H), 4.30 (d, J=14.4 Hz, 1H), 4.57–4.59 (m,
1H), 5.22 (d, J=14.4 Hz, 1H), 6.89 (d, J=8.4 Hz, 2H),
7.28–7.40 (m, 7H); 13C NMR (100 MHz, CDCl3): d=26.2,
29.2, 43.5, 55.2, 66.2, 114.8, 120.1, 127.6, 128.4, 128.7, 136.1,
137.4, 160.7, 174.3; HR-MS (ESI): m/z=336.1013, calcd. for
C18H19NO2SNa [M+Na]+: 336.1034.
5-(4-Aminophenylthio)-1-benzylpyrrolidin-2-one
(9q):
Brown oil; yield: 58 mg (78%); 1H NMR (400 MHz,
CDCl3): d=1.56–1.65 (m, 1H), 2.05–2.38 (m, 3H), 4.29 (d,
J=14.8 Hz, 1H), 4.49–4.51 (m, 1H), 5.18 (d, J=14.8 Hz,
1H), 6.65 (d, J=8.4 Hz, 2H), 7.21 (d, J=8.4 Hz, 2H), 7.26–
7.35 (m, 5H); 13C NMR (100 MHz, CDCl3): d=26.1, 29.2,
43.5, 66.1, 115.5, 116.5, 127.5, 128.4, 128.6, 136.2, 137.5,
147.8, 174.5; HR-MS (ESI): m/z=299.1209, calcd. for
C17H19N2OS [M+H]+: 299.1218.
1-Phenethyl-5-(phenylthio)pyrrolidin-2-one (9r): Yellow
oil; yield: 68 mg (92%); 1H NMR (400 MHz, CDCl3): d=
1.70–1.79 (m, 1H), 2.06–2.18 (m, 2H), 2.29–2.37 (m, 1H),
2.85–2.93 (m, 2H), 3.45–3.52 (m, 1H), 4.03–4.10 (m, 1H),
4.56–4.59 (m, 1H), 7.18–7.36 (m, 10H); 13C NMR (100 MHz,
CDCl3): d=26.8, 29.2, 33.8, 41.9, 68.0,126.6, 128.6, 128.8,
129.0,129.4, 130.8, 135.1, 138.7, 174.6; HR-MS (ESI): m/z=
298.1266, calcd. for C18H20NOS [M+H]+: 298.1266.
5-(4-Methoxyphenylthio)-1-phenethylpyrrolidin-2-one
(9s): Colourless oil; yield: 78 mg (95%); 1H NMR
(400 MHz, CDCl3): d=1.53–1.64 (m, 1H), 1.99–2.34 (m,
3H), 2.83–2.92 (m, 2H), 3.45–3.53 (m, 1H), 3.79 (s, 3H),
Adv. Synth. Catal. 2014, 356, 2627 – 2642
ꢀ 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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