Organic Letters
Letter
Snieckus, V. Modern Arene Chem. 2002, 330. (c) Snieckus, V. Chem.
Rev. 1990, 90, 879.
ASSOCIATED CONTENT
* Supporting Information
Experimental procedures and analytical data for new com-
pounds and products. This material is available free of charge
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S
(8) (a) Anctil, E. J. G.; Snieckus, V. Metal-Catalyzed Cross-Coupling
Reactions, 2nd ed.; Wiley-VCH: Weinheim, 2004; Vol. 2, p 761.
(b) Anctil, E. J. G.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150.
(9) (a) Wang, J.; Qi, W.; Zhang, Y.; Xu, Y. Youji Huaxue 1985, 317.
CAN 104: 186091. (b) Zablocka, M.; Delest, B.; Igau, A.; Skowronska,
A.; Majoral, J. P. Tetrahedron Lett. 1997, 38, 5997.
(10) (a) Sibi, M. P.; Snieckus, V. J. Org. Chem. 1983, 48, 1935.
(b) Alessi, M., Ph.D. Thesis, Queen’s Univesity, Kingston, Ontario,
Canada, 2008.
(11) Wagner, F. F.; Comins, D. L. Tetrahedron 2007, 63, 8065.
(12) An intriguing rationale for this observation is the formation of a
coordinated Al(OBu-t)3-Schwartz reagent species, thus providing
additional steric hindrance in the reduction process.
AUTHOR INFORMATION
Corresponding Author
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Notes
The authors declare no competing financial interest.
(13) By standard desilyation, this yields a 3,4-disubstituted furan
derivative, a not readily accessible class of molecules; see: Bures, E.;
Nieman, J. A.; Yu, S. Y.; Spinazze, P. G.; Bontront, J. L. J.; Hunt, I. R.;
Rauk, A.; Keay, B. A. J. Org. Chem. 1997, 62, 8750.
(14) O’Sullivan, P. S.; De La Vega, J.; Hameka, H. F. Chem. Phys. Lett.
1970, 5, 576.
(15) Besides THF, other solvents such as DME, dioxane, CH2Cl2,
chloroform, and even toluene were found to be suitable solvents for
the in situ reduction process. The above solvent effects are
dramatically different from those observed by Georg;3c see the
Supporting Information.
ACKNOWLEDGMENTS
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We are grateful to Dr. Francoise Sauriol (Queen’s University)
for assistance in NMR spectroscopy, Dr. Jiaxi Wang (Queen’s
Univ.) for discussion of MS spectra, and NSERC Canada
(Discovery Grant) for continuing support of our synthetic
programs.
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