Highly stereospecific, cross-coupling reactions of alkenylsilacyclobutanes

Journal of the American Chemical Society

Volumn 121, Issue 24, 1999, Pages 5821-5822

  Denmark, Scott E ^a   Choi, Jun Young ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; FLUORIDE; ORGANOSILICON DERIVATIVE; PALLADIUM;

ARTICLE; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0344299286     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9908117     Document Type: Article

References (31)

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20. For recent reports on the chemistry of silacyclobutanes see the following: (a) Matsumoto, K.; Oshima, K.; Utimoto, K. J. Synth. Org. Jpn. 1996, 54, 289. (b) Hatanaka, Y.; Watanabe, M.; Onozawa, S.; Tanaka M.; Sakurai, H. J. Org. Chem. 1998, 63, 422. Tanaka, Y.; Yamashita, H.; Tanaka, M. Organometallics 1996, 15, 1524.
21. For recent reports on the chemistry of silacyclobutanes see the following: (a) Matsumoto, K.; Oshima, K.; Utimoto, K. J. Synth. Org. Jpn. 1996, 54, 289. (b) Hatanaka, Y.; Watanabe, M.; Onozawa, S.; Tanaka M.; Sakurai, H. J. Org. Chem. 1998, 63, 422. Tanaka, Y.; Yamashita, H.; Tanaka, M. Organometallics 1996, 15, 1524.
22. E/Z ratios were determined by GC analysis; see Supporting Information.
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26. 2 in DMF solvent gave almost exclusively the reduction product. DMF offered no advantage over THF in successful couplings.
27. This is presumably due to a competitive insertion of the arylpalladium iodide into the silacyclobutane bond if the putative "ate" complex is not formed. Reductive elimination from this intermediate would lead to the reduced arene, A significant exotherm is observed upon mixing 1 with TBAF.
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