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84858103914
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Synthesis of 1: isopropyl alcohol (5 mL) was added to a flask charged with Cs2CO3 (113 mg, 0.35 mmol) and 1-pyreneboronic acid (84 mg, 0.34 mmol, To this suspension was added, PCy 3)AuBr, 95 mg, 0.17 mmol, and the mixture was stirred at 50 °C for 24 h. After it was cooled, the mixture was stripped of solvent in vacuo and extracted into benzene, and the extract was filtered through Celite and taken to dryness by rotary evaporation. The solid was triturated with pentane (to remove traces of isopropyl alcohol, the residual of which was removed by rotary evaporation. The solid was again extracted into benzene, and the extract was filtered through Celite and concentrated to saturation. Vapor diffusion of pentane caused separation of yellow-brown crystals. The supernatant was decanted, and the recrystallization was repeated. The light yellow crystals were collected and dried. Yield: 92 mg (80, 1H NMR 100 MHz; C 6D
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42AuP: C, 60.17; H, 6.24. Found: C, 60.14; H, 6.42.
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de Frémont, P.; Singh, R.; Stevens, E. D.; Petersen, J. L.; Nolan, S. P. Organometallics 2007, 26, 1376-1385.
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de Frémont, P.1
Singh, R.2
Stevens, E.D.3
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Nolan, S.P.5
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84858093922
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-3.
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84858103911
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Crystallographic data for 2: colorless block, crystal dimensions 0.39 × 0.32 × 0.20 mm3, space group P21/c, a, 12.2122(13) Å, b, 12.1108(13) Å, c, 23.060(3) Å, β= 90.024(2)°, V, 3410.6(6) Å3, Z, 4, Pcalcd, 1.532 Mg/m 3, μ(Mo Kα, 4.347 mm-1, data measured on a Broker AXS SMART APEX CCD-based diffractometer (Mo Kα, λ, 0.71073 Å) at 100(2) K, structure solved by direct methods, 28480 reflections collected, 8437 unique reflections (Rint, 0.0398, 8437/0/423 data/restraints/parameters, final R indices (I > 2a(I, R1, 0.0522 and wR2, 0.1273, R indices (all data) R1, 0.0595 and wR2, 0.1310, largest difference peak and hole +7.679 and -3.385 e Å-3
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-3.
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34547241030
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Full details appear in the Supporting Information
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Full details appear in the Supporting Information.
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34547293700
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Calculations employed the Gaussian03 suite of programs: Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A, Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, lyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Pi
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Calculations employed the Gaussian03 suite of programs: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; lyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara. A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
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