Improvements in cross coupling reactions of hypervalent siloxane derivatives

Organic Letters

Volumn 1, Issue 13, 1999, Pages 2137-2140

  Mowery, Molly E ^a   DeShong, Philip ^a  

^a UNIVERSITY OF MARYLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; ORGANOSILICON DERIVATIVE; PALLADIUM; PHENYLTRIMETHOXYSILANE; SILOXANE; THIOPHENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY;

CATALYSIS; LIGANDS; ORGANOSILICON COMPOUNDS; PALLADIUM; SILOXANES; THIOPHENES;

EID: 0033619841     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991186d     Document Type: Article

References (36)

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20. For an example of a copper(I) salt promoted cross coupling reaction between aryl-or heteroarylsilanes and aryl halides in absence of fluoride, see: Ito, H.; Sensui, H.-o.; Arimoto, K.; Miura, K.; Hosomi, A. Chem. Lett. 1997, 639-640 and references therein.
21. 3. Last, Herrmann's catalyst (Herrmann, W. A.; Resinger, C. P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93-96) was synthesized and upon testing failed to give cross coupled adducts.
22. 3. We did not test this particular system using our reaction conditions. For more information, please see: Tamao, K.; Kobayashi, K.; Ito, Y. Tetrahedron Lett. 1989, 30, 6051-6054.
23. 2, please see: Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009-3013.
24. +), 88), 181 (30), 168 (15), 167 (100), 166 (30), 165 (56), 152 (22), 83 (25).
25. This has not been a general trend observed in the literature, and it is a new finding for this particular substrate. At this point in time, we do not have a specific rationalization for this observation. Mechanistic studies with assorted phosphines are underway to elucidate the electronic and stenc roles played by phosphines in the catalytic cycle.
26. 2]. and unfortunately this Pd species only cross-coupled aryl chlorides that were electron-deficient. In the case of electron-neutral or electron-rich aryl chlorides, the reactions were much slower and failed to give satisfactory yields of coupled products. This catalyst system was never tested using our reaction conditions. For more information, please see: Gouda, K.-i.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232-7233.
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29. 3. In all experiments conducted, the ratios of Pd:P were kept identical to that in ref 15.
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33. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369-4378.
34. One ligand. 1-(N,N-dimethylamino)-1′-(dicyclohexylphopshino)-biphenyl, gave poor yields when used with electron-deficient substrates, and with electron-neutral substrates, it was unreactive. A second ligand, 2-(di-tert-butylphosphino)biphenyl, was found to be completely unreactive using 4-chlorotoluene as a substrate.
35. Ligand 1 is commercially available from Strem Chemical Co. and was recrystallized from absolute EtOH prior to use.
36. A report in which alkenyl, alkynyl, aryl, and alkyl silanes are cross-coupled to enol and aryl triflates in the presence of Pd(0) and fluoride ion is available. For more information, please see: Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1990, 31, 2719-2722.