Palladium-catalyzed Mizoroki–Heck coupling reactions using sterically bulky phosphite ligand

de Meijer, 2004 Tamao, 1972, Chem. Soc., 94, 4374, 10.1021/ja00767a075 Tamao, 2002, Chem, 653, 23 Baba, 1976, E-i. Negishi, J. Am. Chem. Soc., 98, 6729, 10.1021/ja00437a067 Negishi, 2007, Bull. Chem. Soc. Jpn, 80, 233, 10.1246/bcsj.80.233 Miyaura, 1979, Tetrahedron Lett., 20, 3437, 10.1016/S0040-4039(01)95429-2 Miyaura, 2002, J. Organomet. Chem., 653, 54, 10.1016/S0022-328X(02)01264-0 Kosugi, 1977, Chem. Lett., 6, 1423, 10.1246/cl.1977.1423 Milstein, 1978, J. Am. Chem. Soc., 100, 3636, 10.1021/ja00479a077 Hatanaka, 1988, J. Org. Chem., 53, 918, 10.1021/jo00239a056 Sonogashira, 1975, Tetrahedron Lett., 50, 4467, 10.1016/S0040-4039(00)91094-3 Sonogashira, 2002, J. Organomet. Chem., 653, 46, 10.1016/S0022-328X(02)01158-0 Mizoroki, 1971, Bull. Chem. Soc. Jpn, 44, 581, 10.1246/bcsj.44.581 Heck, 1972, J. Org. Chem., 37, 2320, 10.1021/jo00979a024 Zapf, 2005, Chem. Commun., 431, 10.1039/b410937f Knowles, 2007, Org. Biomol. Chem., 5, 31, 10.1039/B611547K Shaughnessy, 2000, J. Am. Chem. Soc. 121 (1999) 2123-2332. [18] A. Ehrentraut, A. Zapf, M. Beller, Synlett, 1589 Herrmann, 2002, Angew. Chem. Int. Ed., 41, 1290, 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y Roland, 2006 Ju, 2007, Org. Lett., 9, 4615, 10.1021/ol702058e Beller, 1998 Ju, 2006, Tetrahedron Lett., 47, 8673, 10.1016/j.tetlet.2006.10.017 Moon, 2007, Chem. Lett., 36, 1432, 10.1246/cl.2007.1432 Typical Experimental Procedure: Pd(OAc)2 (3.4mg, 0.015mmol), phosphite 2 (19.0mg, 0.030mmol), aryl iodide (3.0mmol) and alkene (4.0mmol) were combined with K2CO3 (622mg, 4.5mmol) in DMF (10.0mL). The resulting mixture was placed in an oil bath at 120°C for 6h. The reaction was poured into 20mL of saturated aqueous ammonium chloride and extracted with Et2O (3×20mL). The combined ether extracts were washed with brine (60mL), dried over MgSO4, and filtered. The solvent was removed under vacuum. The crude product was purified by flash chromatography (15% ethyl acetate in hexane). Typical Experimental Procedure: Pd(OAc)2 (3.4mg, 0.015mmol), phosphite 2 (19.0mg, 0.030mmol), aryl bromide (3.0mmol) and alkene (4.0mmol) were combined with Na2CO3 (477mg, 4.5mmol) in DMF (10.0mL). The resulting mixture was placed in an oil bath at 140°C for 8h. The reaction was poured into 20mL of saturated aqueous ammonium chloride and extracted with Et2O (3×20mL). The combined ether extracts were washed with brine (60mL), dried over MgSO4, and filtered. The solvent was removed under vacuum. The crude product was purified by flash chromatography (15% ethyl acetate in hexane). van Strijdonck, 1999, Eur. J. Inorg. Chem., 1073, 10.1002/(SICI)1099-0682(199907)1999:7<1073::AID-EJIC1073>3.0.CO;2-T 31P NMR (DMF-d7/CDCl3) phosphite 2: δ124.83; The complex of Pd(OAc)2 and phosphite 2: δ−9.23.