13
2.38 (dt, J = 15.2, 7.6 Hz, 2H CH2), 1.50–1,35 (m, 6H CH2), 0.97–0.86 (m, 3H CH3). C
NMR (101 MHz, CDCl3) δ: 151.28, 143.56 (Pd-C), 137.71, 130.37, 129.92, 128.85, 126.85,
124.26, 55.00, 37.34, 31.20, 29.62, 26.33, 22.49, 14.04. HRMS (ESI-TOF, m/z): 463.0860
C20H26ClN4Pd [M-Cl], calculated: 463.0881.
1
Complex 2d. Light yellow solid, isolated yield 51%. H NMR (300 MHz, CDCl3) δ: 8.98–
8.92 (m, 2H CHAr py), 8.07 (d, J = 8.6 Hz, 4H CHAr Ph), 7.73–7.63 (m, 2H CHAr Ph), 7.54–
7.39 (m, 2H CHAr Ph), 7.30–7.26 (m, 1H CHAr py), 5.00–4.93 (m, 2H N-CH2), 4.03 (s, 3H N-
CH3), 2.39 (dt, J = 15.3, 7.5 Hz, 2H CH2), 1.70 (s, 2H), 1.58–1.31 (m, 6H CH2), 0.91 (t, J =
7.1 Hz, 3H CH3).13C NMR (75 MHz, CDCl3) δ: 151.31, 137.70, 130.76, 129.08, 128.88,
127.53, 127.20, 124.26, 55.06, 37.41, 31.24, 29.59, 26.34, 22.47, 14.01. HRMS (ESI-TOF,
m/z): 539.0878 C26H30ClN4Pd [M-Cl], calculated: 539.0880.
1
Complex 2e. Yellow solid, isolated yield 69%. H NMR (403 MHz, CDCl3) δ: 8.96–8.88 (m,
1H CHAr py), 7.96–7.91 (m, 2H CHAr Ph), 7.72–7.63 (m, 3H CHAr Ph ), 7.60–7.50 (m, 3H
CHAr py), 4.85–4.79 (m, 2H N-CH2), 3.96 (s, 3H N-CH3 ), 2.37–2.26 (m, 4H CH2), 1.08 (t, J
= 7.4 Hz, 2H CH3).13C NMR (75 MHz, CDCl3) δ: 151.18, 143,48 (Pd-C), 137.68, 137.59,
130.29, 129.85, 128.76, 124.21, 54.65, 37.30, 31.53, 19.82, 13.57. HRMS (ESI-TOF, m/z):
435.0554 C18H22ClN4Pd [M-Cl], calculated: 435.0568.
1
Complex 2f. Yellow solid, isolated yield 82%. H NMR (300 MHz, CDCl3) δ: 8.94–8.89 (m,
2H CHAr py), 8.01–7.95 (m, 1H CHAr Ph), 7.82–7.68 (m, 2H CHAr Ph), 7.59–7.51 (m, 2H
CHAr Ph), 7.43–7.26 (m, 5H CHAr Ph), 6.20 (s, 2H N-CH2), 3.95 (s, 3H N-CH3).13C NMR (75
MHz, CDCl3) δ: 151.30, 143.80 (Pd-C), 138.57, 137.73, 133.90, 130.41, 129.99, 129.76,
128.83, 128.79, 126.72, 124.28, 58.64, 37.50. HRMS (ESI-TOF, m/z): 469.0401
C21H20ClN4Pd [M-Cl], calculated: 469.0411.
1
Complex 2g. Light yellow solid, isolated yield 62%. H NMR (403 MHz, CDCl3) δ: 8.95–
8.91 (m, 2H CHAr py), 8.09–8.05 (m, 2H CHAr Ph), 7.65 (dq, J = 2.5, 1.7 Hz, 4H CHAr Ph),
7.51–7.38 (m, 6H CHAr Ph), 7.33–7.27 (m, 2H CHAr py), 6.21 (s, 2H N-CH2), 4.00 (s, 3H N-
CH3). 13C NMR (101 MHz, CDCl3) δ: 151.30, 142.67(Pd-C), 137.75, 133.87, 130.76, 129.77,
128.87, 128.79, 127.82, 127.52, 127.19, 124.22, 58.67, 37.58. HRMS (ESI-TOF, m/z):
545.0720 C27H24ClN4Pd [M-Cl], calculated: 545.0724.
2.3. General Procedure for Suzuki–Miyaura coupling
A boronic acid (2.5 10-4 moles, 1.05 equiv.) and 1 mL of ethanol (99.8%) were placed in a 2
mL glass reactor equipped with a reflux condenser and magnetic stirrer. The reaction mixture
was stirred at 22 °C until complete dissolution of the acid (ca 5 minutes). Then aryl halide (1
equiv.), dodecane (internal standard), a suitable amount of palladium complex and KOH (1.1
equiv.) were added. The reaction mixture was stirred at 22 °C or at 78 °C for 24 hours. The
course of the reaction was monitored by gas chromatography and GC / MS. After completion
of the reaction, 2 mL of distilled water and 2 mL of hexane were added to the reaction
mixture. The organic phase was washed with water (2 2 mL). The product was isolated
4