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Review:, 2nd ed, de Meijere, A, Diederich, F, Eds, Wiley-VCH Verlag GmbH & Co, Weinheim, Chapter 3
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Review: Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH Verlag GmbH & Co.: Weinheim, 2004; Vol. 1, Chapter 3.
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Mitchell, T.N.1
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Recent applications in natural products total synthesis: (a) Nicolaou, K. C.; Koftis, T. V.; Vyskocil, S.; Petrovic, G.; Tang, W.; Frederick, M. O.; Chen, D. Y.-K.; Li, Y.; Ling, T.; Yamada, Y. M. A. J. Am. Chem. Soc. 2006, 128, 2859-2872.
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Recent applications in natural products total synthesis: (a) Nicolaou, K. C.; Koftis, T. V.; Vyskocil, S.; Petrovic, G.; Tang, W.; Frederick, M. O.; Chen, D. Y.-K.; Li, Y.; Ling, T.; Yamada, Y. M. A. J. Am. Chem. Soc. 2006, 128, 2859-2872.
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(a) Bhatt, R. K.; Shin, D. S.; Falck, J. R.; Mioskowski, C. Tetrahedron Lett. 1992, 33, 4885-4888.
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Bhatt, R.K.1
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Linderman, R. J.; Graves, D. M.; Kwochka, W. R.; Ghannam, A. F.; Anklekar, T. V. J. Am. Chem. Soc. 1990, 112, 7438-7439.
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Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973-5982.
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Falck, J.R.1
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Ye, J.; Bhatt, R. K.; Falck, J. R. Tetrahedron Lett. 1993, 34, 8007-8010.
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Ye, J.1
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Falck, J. R.; Barma, D.; Mohapatra, S.; Bandyopadhyay, A.; Reddy, K. M.; Qi, J.; Campbell, W. Bioorg. Med. Chem. Lett. 2004, 14, 4987-4990.
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Falck, J.R.1
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Reddy, K.M.5
Qi, J.6
Campbell, W.7
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Recent examples of alternative chiral allylic alcohol syntheses: (a) Berkessel, A.; Roland, K.; Neudoerfl, J. M. Org. Lett. 2006, 8, 4195-4198.
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Recent examples of alternative chiral allylic alcohol syntheses: (a) Berkessel, A.; Roland, K.; Neudoerfl, J. M. Org. Lett. 2006, 8, 4195-4198.
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(c) Hilt, G.; Hess, W.; Harms, K. Org. Lett. 2006, 8, 3287-3290.
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Org. Lett
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Hilt, G.1
Hess, W.2
Harms, K.3
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33746403241
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Recent examples of alternative chiral benzylic alcohol syntheses: (a) Yang, S.-D.; Shi, Y.; Sun, Z.-H.; Zhao, Y.-B.; Liang, Y.-M. Tetrahedron: Asymmetry 2006, 17, 1895-1900.
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Recent examples of alternative chiral benzylic alcohol syntheses: (a) Yang, S.-D.; Shi, Y.; Sun, Z.-H.; Zhao, Y.-B.; Liang, Y.-M. Tetrahedron: Asymmetry 2006, 17, 1895-1900.
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(b) Zhu, D.; Yang, Y.; Hua, L. J. Org. Chem. 2006, 71, 4202-4205.
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J. Org. Chem
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Zhu, D.1
Yang, Y.2
Hua, L.3
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(c) Grasa, G. A.; Zanotti-Gerosa, A.; Hems, W. P. J. Organomet. Chem. 2006, 691, 2332-2334.
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J. Organomet. Chem
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Grasa, G.A.1
Zanotti-Gerosa, A.2
Hems, W.P.3
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Since CuTC is used in stoichiometric amounts and apparently consumed to some extent, a reviewer suggested the term promoter instead of catalyst
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Since CuTC is used in stoichiometric amounts and apparently consumed to some extent, a reviewer suggested the term promoter instead of catalyst.
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Catalysis or promotion ot the Stille reaction by copper salts in combination with other transition metals or alone is well established: (a) Liebeskind. L. S, Fengl, R. W. J. Org. Chem. 1990, 55, 5359-5364
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Catalysis or promotion ot the Stille reaction by copper salts in combination with other transition metals or alone is well established: (a) Liebeskind. L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359-5364.
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(c) Piers, E.; McEachern, E. J.; Burns, P. A. J. Org. Chem. 1995, 60, 2322-2323.
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J. Org. Chem
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Piers, E.1
McEachern, E.J.2
Burns, P.A.3
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Transmetalation of organostannanes with higher order cuprates is also known: Behling, J. R.; Babiak, K. A.; Ng, J. S.; Campbell, A. L.; Moretti, R.; Koerner, M.; Lipshutz, B. H. J. Am. Chem. Soc. 1988, 110, 2641-2643.
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Transmetalation of organostannanes with higher order cuprates is also known: Behling, J. R.; Babiak, K. A.; Ng, J. S.; Campbell, A. L.; Moretti, R.; Koerner, M.; Lipshutz, B. H. J. Am. Chem. Soc. 1988, 110, 2641-2643.
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We speculate that CuTC is more effective than other copper salts because it is bidentate and can establish a highly coordinated intermediate, e.g, i, that resists β-elimination. This may explain, in part, why simple aryl iodides and 1-iodocyclohexene are satisfactory coupling partners, in contrast to the experience of Allred and Liebeskind see ref. 15, Diagram presented
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We speculate that CuTC is more effective than other copper salts because it is bidentate and can establish a highly coordinated intermediate, e.g., i, that resists β-elimination. This may explain, in part, why simple aryl iodides and 1-iodocyclohexene are satisfactory coupling partners, in contrast to the experience of Allred and Liebeskind (see ref. 15). (Diagram presented)
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The Liebeskind laboratory developed CuTC and adroitly exploited it for the cross-coupling of organostannanes with aryl and alkenyl iodides: Allred, G. D, Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749
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The Liebeskind laboratory developed CuTC and adroitly exploited it for the cross-coupling of organostannanes with aryl and alkenyl iodides: Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749.
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Little, if any, tri-n-butylstannyl iodide or distannane is observed in the crude product at the end of the reaction. In light of the report by Allred and Liebeskind (ref. 15) that tri-n-butylstannyl thiophene-2-carboxylate is produced in their reactions, we speculate that the tri-n-butylstannyl byproduct is sequestered in this form. It would follow, therefore, that stoichiometric amounts of CuTC would be required, and this is what we found empirically to achieve maximum yields.
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Little, if any, tri-n-butylstannyl iodide or distannane is observed in the crude product at the end of the reaction. In light of the report by Allred and Liebeskind (ref. 15) that tri-n-butylstannyl thiophene-2-carboxylate is produced in their reactions, we speculate that the tri-n-butylstannyl byproduct is sequestered in this form. It would follow, therefore, that stoichiometric amounts of CuTC would be required, and this is what we found empirically to achieve maximum yields.
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Lewis acid catalyzed Newman-Kwart rearrangement: Fujii, K.; Shuto, Y.; Kinoshita, Y. Agric. Biol. Chem. 1990, 54, 2379-2384.
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Lewis acid catalyzed Newman-Kwart rearrangement: Fujii, K.; Shuto, Y.; Kinoshita, Y. Agric. Biol. Chem. 1990, 54, 2379-2384.
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Mee, S. P. H.; Lee, V.; Baldwin, J. E. Chem. Eur. J. 2005, 11, 3294-3308.
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Chem. Eur. J
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Mee, S.P.H.1
Lee, V.2
Baldwin, J.E.3
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Jäger, V.; Schröter, D.; Koppenhoefer, B. Tetrahedron 1991, 47, 2195-2210
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(1991)
Tetrahedron
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Jäger, V.1
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(a) Dieter, R. K.; Oba, G.; Chandupatla, K. R.; Topping, C. M.; Lu, K.; Watson, R. T. J. Org. Chem. 2004, 69, 3076-3086.
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J. Org. Chem
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Dieter, R.K.1
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Topping, C.M.4
Lu, K.5
Watson, R.T.6
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(b) Tomooka, K.; Shimizu, H.; Nakai, T. J. Organomet. Chem. 2001, 624, 364-366.
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J. Organomet. Chem
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Tomooka, K.1
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