LETTER
Addition of Arylboronic Acids to Nitriles in Aqueous Media
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.38 (d, J = 6.8 Hz, 2 H), 7.79 (t, J = 6.0 Hz, 1 H), 8.02 (t, J = 7.6 Hz, 4 H), 7.57 (t, J = 7.4 Hz, 2 H), 7.79–7.81 (m, 4
1
3
J = 7.6 Hz, 1 H), 8.27 (t, J = 7.6 Hz, 1 H), 8.35 (d, J = 7.6
Hz, 1 H), 8.43 (d, J = 7.6 Hz, 1 H), 9.20 (d, J = 4.8 Hz, 1 H).
H) ppm. C NMR (100 MHz, CDCl ): d = 128.2, 130.0,
3
+
132.3, 137.5, 196.7 ppm. MS (ESI+): m/z = 183.1 [M + H] ,
1
3
+
+
C NMR (100 MHz, MeOD): d = 17.3, 21.1, 70.6, 70.8,
2.2, 75.0, 92.1, 98.8, 124.2, 125.3, 127.3, 128.6, 131.8,
39.4, 141.4, 141.8, 145.5, 149.8, 154.1, 155.5, 157.8,
89.4. HRMS (ESI+): m/z calcd for C H N FeClPd [M –
205.1 [M + Na] , 221.0 [M + K] .
1
7
1
1
Compound 3j: H NMR (400 MHz, CDCl ): d = 7.52–7.56
3
(m, 2 H), 7.66–7.70 (m, 1 H), 7.80–7.83 (m, 2 H), 8.00–8.04
1
3
(m, 2 H), 8.17–8.19 (m, 2 H) ppm. C NMR (100 MHz,
2
9
26
3
+
Cl] : 578.0511; found: 578.0518. IR (KBr): n = 3018, 1633,
CDCl ): d = 119.7 (q, J = 324.1 Hz), 128.8, 130.2, 130.7,
3
1600, 1473, 1438, 1368, 1227, 1153, 1106, 1073, 1027, 810,
130.9, 133.8, 134.2, 135.9, 144.8, 194.6 ppm. MS (ESI+):
m/z = 337.4 [M + Na] , 353.7 [M + K] . HRMS (ESI+): m/z
–
1
+
+
776, 494 cm .
1
+
Compound 3a: H NMR (400 MHz, CDCl ): d = 2.40 (s, 3
H), 4.26 (s, 2 H), 7.23–7.32 (m, 7 H), 7.91 (d, J = 7.4 Hz, 2
calcd for C H F SO [M + H] : 315.0303; found: 315.0300.
3
14
9
3
3
1
Compound 3k: H NMR (400 MHz, CDCl ): d = 6.92–6.96
(m, 2 H), 7.46–7.49 (m, 2 H), 7.55–7.59 (m, 1 H), 7.75–7.80
(m, 4 H) ppm. C NMR (100 MHz, CDCl ): d = 115.4,
128.3, 129.7, 129.9, 132.2, 133.1, 138.0, 160.6, 196.7 ppm.
3
1
3
H) ppm. C NMR (100 MHz, CDCl ): d = 21.7, 45.4, 126.8,
3
1
3
128.6, 128.8, 129.3, 129.4, 134.1, 134.8, 144.0, 197.3 ppm.
3
+
+
MS (ESI+): m/z = 211.1 [M + H] , 233.1 [M + Na] , 249.0
+
+
+
[M + K] .
MS (ESI+): m/z = 199.2 [M + H] , 221.1 [M + Na] , 237.1
1
+
Compound 3c: H NMR (400 MHz, CDCl ): d = 3.86 (s, 3
H), 4.23 (s, 2 H), 6.91–6.94 (m, 2 H), 7.24–7.33 (m, 5 H),
[M + K] .
3
1
Compound 3l: H NMR (400 MHz, CDCl ): d = 5.28 (s, 2
H), 6.94–7.01 (m, 3 H), 7.26–7.31 (m, 2 H), 7.48–7.52 (m, 2
H), 7.60–7.64 (m, 1 H), 8.00–8.02 (m, 2 H) ppm. C NMR
3
1
3
7.98–8.00 (m, 2 H) ppm. C NMR (100 MHz, CDCl3):
1
3
d = 45.3, 55.5, 113.8, 126.8, 128.6, 129.4, 129.7, 131.0,
+
135.0, 163.5, 196.2 ppm. MS (ESI+): m/z = 227.3 [M + H] ,
(100 MHz, CDCl ): d = 70.8, 114.8, 121.7, 128.2, 128.8,
3
+
+
249.2 [M + Na] , 265.2 [M + K] .
129.6, 133.9, 134.6, 158.0, 194.6 ppm. MS (ESI+): m/z =
1
+
+
+
Compound 3e: H NMR (400 MHz, CDCl ): d = 4.27 (s, 2
213.1 [M + H] , 235.0 [M + Na] , 251.0 [M + K] .
3
1
H), 7.25–7.28 (m, 5 H), 7.32–7.36 (m, 2 H), 8.05–8.07 (m, 2
Compound 3m: H NMR (400 MHz, CDCl ): d = 7.53 (t,
J = 7.7, 2 H), 6.64–7.68 (m, 1 H), 7.79–7.81 (m, 2 H), 7.93–
7.96 (m, 2 H), 8.33–8.36 (m, 2 H) ppm. C NMR (100 MHz,
3
H) ppm. 13C NMR (100 MHz, CDCl ): d = 45.6, 120.3 (q,
3
1
3
J = 257.4 Hz), 120.4, 127.1, 128.8, 129.4, 130.6, 134.1,
+
134.8, 152.7, 196.0 ppm. MS (ESI+): m/z = 281.0 [M + H] ,
CDCl ): d = 123.6, 128.7, 130.1, 130.7, 133.5, 136.3, 142.9,
3
+
+
+
303.1 [M + Na] , 319.0 [M + K] .
149.9, 194.8 ppm. MS (ESI+): m/z = 228.4 [M + H] , 250.3
[M + Na] .
1
+
Compound 3f: H NMR (400 MHz, CDCl ): d = 7.47 (t,
3
Synlett 2007, No. 19, 3063–3067 © Thieme Stuttgart · New York