Catalytic Functionalization of Carbon - Hydrogen and Carbon - Carbon Bonds in Protic Media

Accounts of Chemical Research

Volumn 31, Issue 9, 1998, Pages 550-557

  Sen, Ayusman ^a,b,c,d  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b University of Chicago ^*  (United States)

^c UNIVERSITY OF CHICAGO   (United States)

^d CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000521793     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar970290x     Document Type: Article

References (97)

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5. Recent reviews: (a) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Herrmann, W. A., Cornils, B., Eds.; VCH: Weinheim, Germany, 1996; Vol. 2, pp 1081-92. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987-1007. (c) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154-62. (d) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325-38. (e) Fierro, J. L. G. Catalysis Lett. 1993, 22, 67-91. (f) Srivastava, R. D.; Zhou, P.; Stiegel, G. J.; Rao, V. U. S.; Cinquegrane, G. Catalysis (London) 1992, 9, 183-228. (g) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995.
6. Recent reviews: (a) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Herrmann, W. A., Cornils, B., Eds.; VCH: Weinheim, Germany, 1996; Vol. 2, pp 1081-92. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987-1007. (c) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154-62. (d) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325-38. (e) Fierro, J. L. G. Catalysis Lett. 1993, 22, 67-91. (f) Srivastava, R. D.; Zhou, P.; Stiegel, G. J.; Rao, V. U. S.; Cinquegrane, G. Catalysis (London) 1992, 9, 183-228. (g) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995.
7. Recent reviews: (a) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Herrmann, W. A., Cornils, B., Eds.; VCH: Weinheim, Germany, 1996; Vol. 2, pp 1081-92. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987-1007. (c) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154-62. (d) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325-38. (e) Fierro, J. L. G. Catalysis Lett. 1993, 22, 67-91. (f) Srivastava, R. D.; Zhou, P.; Stiegel, G. J.; Rao, V. U. S.; Cinquegrane, G. Catalysis (London) 1992, 9, 183-228. (g) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995.
8. Recent reviews: (a) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Herrmann, W. A., Cornils, B., Eds.; VCH: Weinheim, Germany, 1996; Vol. 2, pp 1081-92. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987-1007. (c) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154-62. (d) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325-38. (e) Fierro, J. L. G. Catalysis Lett. 1993, 22, 67-91. (f) Srivastava, R. D.; Zhou, P.; Stiegel, G. J.; Rao, V. U. S.; Cinquegrane, G. Catalysis (London) 1992, 9, 183-228. (g) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995.
9. Recent reviews: (a) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Herrmann, W. A., Cornils, B., Eds.; VCH: Weinheim, Germany, 1996; Vol. 2, pp 1081-92. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987-1007. (c) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154-62. (d) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325-38. (e) Fierro, J. L. G. Catalysis Lett. 1993, 22, 67-91. (f) Srivastava, R. D.; Zhou, P.; Stiegel, G. J.; Rao, V. U. S.; Cinquegrane, G. Catalysis (London) 1992, 9, 183-228. (g) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995.
10. Recent reviews: (a) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Herrmann, W. A., Cornils, B., Eds.; VCH: Weinheim, Germany, 1996; Vol. 2, pp 1081-92. (b) Crabtree, R. H. Chem. Rev. 1995, 95, 987-1007. (c) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154-62. (d) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325-38. (e) Fierro, J. L. G. Catalysis Lett. 1993, 22, 67-91. (f) Srivastava, R. D.; Zhou, P.; Stiegel, G. J.; Rao, V. U. S.; Cinquegrane, G. Catalysis (London) 1992, 9, 183-228. (g) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995.
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18. Recent representative publications: (a) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2016-23. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-31. (c) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699-701. (d) Rondon, D.; Chaudret, B.; He, X.-D.; Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671-76. (e) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717-19. (f) Bunel, E.; Burger, B. J.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976-78. (g) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222-27. (h) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679-81. (i) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471-73. (j) Dufaud, V.; Basset, J.-M. Angew. Chem., Int. Ed. Engl. 1998, 37, 806-10.
19. Recent representative publications: (a) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2016-23. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-31. (c) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699-701. (d) Rondon, D.; Chaudret, B.; He, X.-D.; Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671-76. (e) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717-19. (f) Bunel, E.; Burger, B. J.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976-78. (g) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222-27. (h) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679-81. (i) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471-73. (j) Dufaud, V.; Basset, J.-M. Angew. Chem., Int. Ed. Engl. 1998, 37, 806-10.
20. Recent representative publications: (a) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2016-23. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-31. (c) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699-701. (d) Rondon, D.; Chaudret, B.; He, X.-D.; Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671-76. (e) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717-19. (f) Bunel, E.; Burger, B. J.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976-78. (g) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222-27. (h) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679-81. (i) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471-73. (j) Dufaud, V.; Basset, J.-M. Angew. Chem., Int. Ed. Engl. 1998, 37, 806-10.
21. Recent representative publications: (a) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2016-23. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-31. (c) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699-701. (d) Rondon, D.; Chaudret, B.; He, X.-D.; Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671-76. (e) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717-19. (f) Bunel, E.; Burger, B. J.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976-78. (g) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222-27. (h) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679-81. (i) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471-73. (j) Dufaud, V.; Basset, J.-M. Angew. Chem., Int. Ed. Engl. 1998, 37, 806-10.
22. Recent representative publications: (a) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2016-23. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-31. (c) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699-701. (d) Rondon, D.; Chaudret, B.; He, X.-D.; Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671-76. (e) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717-19. (f) Bunel, E.; Burger, B. J.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976-78. (g) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222-27. (h) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679-81. (i) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471-73. (j) Dufaud, V.; Basset, J.-M. Angew. Chem., Int. Ed. Engl. 1998, 37, 806-10.
23. Recent representative publications: (a) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2016-23. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-31. (c) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699-701. (d) Rondon, D.; Chaudret, B.; He, X.-D.; Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671-76. (e) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717-19. (f) Bunel, E.; Burger, B. J.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976-78. (g) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222-27. (h) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679-81. (i) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471-73. (j) Dufaud, V.; Basset, J.-M. Angew. Chem., Int. Ed. Engl. 1998, 37, 806-10.
24. Recent representative publications: (a) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2016-23. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-31. (c) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699-701. (d) Rondon, D.; Chaudret, B.; He, X.-D.; Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671-76. (e) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717-19. (f) Bunel, E.; Burger, B. J.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976-78. (g) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222-27. (h) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679-81. (i) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471-73. (j) Dufaud, V.; Basset, J.-M. Angew. Chem., Int. Ed. Engl. 1998, 37, 806-10.
25. Recent representative publications: (a) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2016-23. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-31. (c) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699-701. (d) Rondon, D.; Chaudret, B.; He, X.-D.; Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671-76. (e) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717-19. (f) Bunel, E.; Burger, B. J.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976-78. (g) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222-27. (h) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679-81. (i) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471-73. (j) Dufaud, V.; Basset, J.-M. Angew. Chem., Int. Ed. Engl. 1998, 37, 806-10.
26. Recent representative publications: (a) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2016-23. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-31. (c) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699-701. (d) Rondon, D.; Chaudret, B.; He, X.-D.; Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671-76. (e) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717-19. (f) Bunel, E.; Burger, B. J.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976-78. (g) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222-27. (h) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679-81. (i) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471-73. (j) Dufaud, V.; Basset, J.-M. Angew. Chem., Int. Ed. Engl. 1998, 37, 806-10.
27. Recent representative publications: (a) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2016-23. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-31. (c) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699-701. (d) Rondon, D.; Chaudret, B.; He, X.-D.; Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671-76. (e) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717-19. (f) Bunel, E.; Burger, B. J.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976-78. (g) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222-27. (h) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1986, 108, 4679-81. (i) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471-73. (j) Dufaud, V.; Basset, J.-M. Angew. Chem., Int. Ed. Engl. 1998, 37, 806-10.
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31. Reviews: (a) Armentrout, P. B. In Selective Hydrocarbon Oxidation and Functionalization; Davies, J. A., Watson, P. L., Greenberg, A., Liebman, J. F., Eds.; VCH: New York, 1990; pp 467-533. (b) Armentrout, P. B.; Beauchamp, J. L. Acc. Chem. Res. 1989, 22, 315-21. (c) Eller, K.; Schwarz, H. Chem. Rev. 1991, 91, 1121-77. (d) Schwarz, H. Acc. Chem. Res. 1989, 22, 282-87.
32. Reviews: (a) Armentrout, P. B. In Selective Hydrocarbon Oxidation and Functionalization; Davies, J. A., Watson, P. L., Greenberg, A., Liebman, J. F., Eds.; VCH: New York, 1990; pp 467-533. (b) Armentrout, P. B.; Beauchamp, J. L. Acc. Chem. Res. 1989, 22, 315-21. (c) Eller, K.; Schwarz, H. Chem. Rev. 1991, 91, 1121-77. (d) Schwarz, H. Acc. Chem. Res. 1989, 22, 282-87.
33. Reviews: (a) Armentrout, P. B. In Selective Hydrocarbon Oxidation and Functionalization; Davies, J. A., Watson, P. L., Greenberg, A., Liebman, J. F., Eds.; VCH: New York, 1990; pp 467-533. (b) Armentrout, P. B.; Beauchamp, J. L. Acc. Chem. Res. 1989, 22, 315-21. (c) Eller, K.; Schwarz, H. Chem. Rev. 1991, 91, 1121-77. (d) Schwarz, H. Acc. Chem. Res. 1989, 22, 282-87.
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35. Reviews: (a) Sen, A. Platinum Metals Rev. 1991, 35, 126-32. (b) Shilov, A. E. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reidel: Dordrecht, The Netherlands, 1984; Chapt. V.
36. Reviews: (a) Sen, A. Platinum Metals Rev. 1991, 35, 126-32. (b) Shilov, A. E. Activation of Saturated Hydrocarbons by Transition Metal Complexes; Reidel: Dordrecht, The Netherlands, 1984; Chapt. V.
37. Reviews: (a) Rothwell, I. P. In Selective Hydrocarbon Oxidation and Functionalization; Davies, J. A., Watson, P. L., Greenberg, A., Liebman, J. F., Eds.; VCH: New York, 1990; pp 43-78. (b) Watson, P. L. In Selective Hydrocarbon Oxidation and Functionalization; Davies, J. A., Watson, P. L., Greenberg, A., Liebman, J. F., Eds.; VCH: New York, 1990; pp 79-112. (c) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325-87. Specific recent examples: (d) Holtcamp, M. W.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1997, 119, 848-49. (e) Schaller, C. P.; Cummins, C. C.; Wolczanski, P. T. J. Am. Chem. Soc. 1996, 118, 591-611. (f) Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970-72.
38. Reviews: (a) Rothwell, I. P. In Selective Hydrocarbon Oxidation and Functionalization; Davies, J. A., Watson, P. L., Greenberg, A., Liebman, J. F., Eds.; VCH: New York, 1990; pp 43-78. (b) Watson, P. L. In Selective Hydrocarbon Oxidation and Functionalization; Davies, J. A., Watson, P. L., Greenberg, A., Liebman, J. F., Eds.; VCH: New York, 1990; pp 79-112. (c) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325-87. Specific recent examples: (d) Holtcamp, M. W.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1997, 119, 848-49. (e) Schaller, C. P.; Cummins, C. C.; Wolczanski, P. T. J. Am. Chem. Soc. 1996, 118, 591-611. (f) Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970-72.
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