Electronic Resource
Carbon(sp 3 )???Fluorine Bond???Forming Reductive Elimination from Palladium(IV) Complexes
العنوان: | Carbon(sp 3 )???Fluorine Bond???Forming Reductive Elimination from Palladium(IV) Complexes |
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المؤلفون: | Department of Chemistry, University of Michigan, 930 N. University Ave, Ann Arbor, MI 48109 (USA), Racowski, Joy M., Gary, J. Brannon, Sanford, Melanie S. |
بيانات النشر: | WILEY???VCH Verlag 2012-04-04T18:42:09Z WITHHELD_13_MONTHS 2012-04-04T18:42:09Z 2012-04-02 |
نوع الوثيقة: | Electronic Resource |
URL: | |
الاتاحة: | Open access content. Open access content IndexNoFollow |
Other Numbers: | EYM oai:deepblue.lib.umich.edu:2027.42/90520 0044-8249 1521-3757 10.1002/ange.201107816 Angewandte Chemie A. J. Canty, Dalton Trans. 2009, 10409 ??? 10417; N. D. Ball, J. B. Gary, Y. Ye, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 7577 ??? 7584. V. V. Grushin, Chem. Eur. J. 2002, 8, 1006 ??? 1014. ?? P. Sehnal, R. J. K. Taylor, I. J. S. Fairlamb, Chem. Rev. 2010, 110, 824 ??? 889; J. M. Racowski, M. S. Sanford, Top. Organomet. Chem. 2010, 53, 63 ??? 84. D. W. Kim, C. E. Song, D. Y. Chi, J. Org. Chem. 2003, 68, 4281 ??? 4285; J. A. Wilkinson, Chem. Rev. 1992, 92, 505 ??? 519. Thermolysis of complexes 2 and 4 gave complex and intractable mixtures of products. We hypothesize that this result may be due to decomposition of the initially formed reductive elimination products (analogues of 6 and 7 ), because these Pd II species would contain highly labile H 2 O and/or OTf ligands. J. F. Hartwig, Organotransition Metal Chemistry: From Bonding to Catalysis, University Science Books, Sausalito, 2010, pp.??? 332 ??? 333; J. F. Hartwig, Nature 2008, 455, 314 ??? 322; A. J. Canty, Acc. Chem. Res. 1992, 25, 83 ??? 90. Reductive elimination from 5 is inhibited by added NMe 4 F. For example, k was 5.75??10 ???4 ???s ???1 without added NMe 4 F and 3.26??10 ???4 ???s ???1 in the presence of 2.4???equivalents of NMe 4 F. This result is consistent with reductive elimination from 5 proceeding by an analogous pathway to that proposed for 3. R. H. Crabtree, The Organometallic Chemistry of Transition Metals, Wiley, Hoboken, NJ, 2005; P. R. Mitchell, P. V. Parish, J. Chem. Educ. 1969, 46, 811 ??? 814. M.???J. Frisch, et???al. Gaussian 09, Gaussian Inc.: Wallingford, CT, 2009 (see the Supporting Information for the complete reference). Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215 ??? 241. W. J. Stevens, H. Basch, M. Krauss, J. Chem. Phys. 1984, 81, 6026 ??? 6033. W. J. Stevens, M. Krauss, H. Basch, P. G. Jasien, Can. J. Chem. 1992, 70, 612 ??? 630. A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2009, 113, 6378 ??? 6396. We were unable to optimize a unique transition state corresponding to C(sp 3 )???F coupling from 8 ???I. All attempts resulted in the same transition state structure found for 8. CCDC???852596 ( 4 ) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. For reviews, see: K. M. Engle, T. S. Mei, X. Wang, J. Q. Yu, Angew. Chem. 2011, 123, 1514 ??? 1528; Angew. Chem. Int. Ed. 2011, 50, 1478 ??? 1491; T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470 ??? 477; V. V. Grushin, Acc. Chem. Res. 2010, 43, 160 ??? 171; A. Vigalok, A. W. Kaspi, Top. Organomet. Chem. 2010, 31, 19 ??? 38. For Pd 0/II catalysis for C(sp 2 )???F and allylic C(sp 3 )???F bond formation, see: T. J. Maimone, P. J. Milner, T. Kinzel, Y. Zhang, M. K. Takase, S. N. Buchwald, J. Am. Chem. Soc. 2011, 133, 18106 ??? 18109; M. H. Katcher, A. Sha, A. G. Doyle, J. Am. Chem. Soc. 2011, 133, 15902 ??? 15905; T. No??l, T. J. Maimone, S. L. Buchwald, Angew. Chem. 2011, 123, 9062 ??? 9065; Angew. Chem. Int. Ed. 2011, 50, 8900 ??? 8903; C. Hollingworth, A. Hazari, M. N. Hopkinson, M. Tredwell, E. Benedetto, M. Huiban, A. D. Gee, J. M. Brown, V. Gouverneur, Angew. Chem. 2011, 123, 2661 ??? 2665; Angew. Chem. Int. Ed. 2011, 50, 2613 ??? 2617; M. H. Katcher, A. G. Doyle, J. Am. Chem. Soc. 2010, 132, 17402 ??? 17404; D. A. Watson, M. Su, G. Teverovskiy, Y. Zhang, J. Garcia???Fortanet, T. Kinzel, S. L. Buchwald, Science 2009, 325, 1661 ??? 1664. For other recent examples of metal???catalyzed fluorination reactions, see: T. Xu, X. Mu, H. Peng, G. Liu, Angew. Chem. 2011, 123, 8326 ??? 8329; Angew. Chem. Int. Ed. 2011, 50, 8176 ??? 8179; P. Tang, T. Furuya, T. Ritter, J. Am. Chem. Soc. 2010, 132, 12150 ??? 12154; J. A. Kalow, A. G. Doyle, J. Am. Chem. Soc. 2010, 132, 3268 ??? 3269; for a review on Au???catalyzed fluorination reactions, see: M. N. Hopkinson, A. G. Gee, V. Gouverneur, Isr. J. Chem. 2010, 50, 675 ??? 690. For Pd???catalyzed C???H fluorination with F + reagents, see: K. S. L. Chan, M. Wasa, X. Wang, J. Q. Yu, Angew. Chem. 2011, 123, 9247 ??? 9250; Angew. Chem. Int. Ed. 2011, 50, 9081 ??? 9084; X. Wang, T. S. Mei, J. Q. Yu, J. Am. Chem. Soc. 2009, 131, 7520 ??? 7521; K. L. Hull, W. Q. Anani, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 7134 ??? 7135. For Pd???catalyzed olefin aminofluorination with F + reagents, see: T. Wu, G. Yin, G. Liu, J. Am. Chem. Soc. 2009, 131, 16354 ??? 16355. For stoichiometric aryl???F coupling from Pd II /F +, see: T. Furuya, T. Ritter, Angew. Chem. 2008, 120, 6082 ??? 6085; Angew. Chem. Int. Ed. 2008, 47, 5993 ??? 5996. T. Furuya, D. Benitez, E. Tkatchouk, A. E. Strom, P. Tang, W. A. Goddard ??? III, T. Ritter, J. Am. Chem. Soc. 2010, 132, 3793 ??? 3807; N. D. Ball, M. S. Sanford, J. Am. Chem. Soc. 2009, 131, 3796 ??? 3797. A. W. Kaspi, I. Goldberg, A. Vigalok, J. Am. Chem. Soc. 2010, 132, 10626 ??? 10627. S. B. Zhao, J. J. Becker, M. R. Gagne, Organometallics 2011, 30, 3926 ??? 3929. For a recent example of C(sp 3 )???F bond???forming reductive elimination from in???situ generated Au III complexes, see: N. P. Mankad, F. D. Toste, Chem. Sci. 2012, 3, 72 ??? 76. For the microscopic reverse oxidative addition of C(sp 3 )???F bonds, see: J. Choi, D. Y. Wang, S. Kundu, Y. Choliy, T. J. Emge, K. Krough???Jespersen, A. S. Goldman, Science 2011, 332, 1545 ??? 1548. J. C??mpora, J. A. L??pez, P. Palma, D. del???Rio, E. Carmona, P. Valerga, C. Graiff, A. Tiripicchio, Inorg. Chem. 2001, 40, 4116 ??? 4126. For use of NFTPT to access high oxidation state Pd complexes, see: J. M. Racowski, N. D. Ball, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 18022 ??? 18025; 894446072 |
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