Rhodium-mediated decarboxylative conjugate addition of fluorinated benzoic acids: stoichiometric and catalytic transformations

Angewandte Chemie - International Edition

Volumn 48, Issue 36, 2009, Pages 6726-6730

  Sun, Zhong Ming ^a   Zhao, Pinjing ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

Carboxylic acids; Conjugate addition; Decarboxylation; Heck mizoroki reaction; Rhodium

Indexed keywords

ACRYLAMIDES; ACRYLIC ESTER; ARYLATIONS; BENZOIC ACID; BINAPHTHYL; BISPHOSPHINE; CATALYTIC TRANSFORMATION; CONJUGATE ADDITION; DECARBOXYLATION; DIFLUORINATED; DIOXOLANE; HECK-MIZOROKI; HECK-MIZOROKI REACTION;

AMIDES; CARBOXYLATION; CARBOXYLIC ACIDS; ESTERS; ORGANIC ACIDS;

RHODIUM;

BENZOIC ACID DERIVATIVE; FLUORINE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DECARBOXYLATION; STEREOISOMERISM;

BENZOIC ACIDS; CATALYSIS; DECARBOXYLATION; FLUORINE; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM;

EID: 70349906980     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901097     Document Type: Article

References (53)

1. For reviews, see: a) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061;
2. b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171-196.
3. For reviews, see: a) K. Yoshida, T. Hayashi in Modern RhodiumCatalyzed Organic Reactions (Ed.: P.A. Evans), Wiley-VCH, Weinheim, 2005, chap. 3;
4. b) T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829-2844;
5. c) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196; for mechanistic studies on rhodiumcatalyzed 1,4-addition reactions of aryl boronic acids, see:
6. d) M. Sakai, H. Hayashi, N. Miyaura, Organometallics 1997, 16, 4229-4231;
7. e) T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052-5058.
8. For the generation of rhodium(I) aryl and alkynyl nucleophiles for catalytic conjugate addition through ß-carbon elimination from rhodium(I) tertiary alkoxides, see: a) T. Nishimura, T. Katoh, T. Hayashi, M. Sakai, H. Hayashi, Angew. Chem. 2007, 119, 5025-5027;
9. Angew. Chem. Int. Ed. 2007, 46, 4937-4939;
10. b) T. Nishimura, T. Katoh, K. Takatsu, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2007, 129, 14158-14159;
11. c) R. Shintani, K. Takatsu, T. Katoh, T. Nishimura, T. Hayashi, Angew. Chem. 2008, 120, 1469-1471;
12. Angew. Chem. Int. Ed. 2008, 47, 14471449.
13. For a recent review, see: L. J. Gooßen, N. Rodríguez, K. Gooßen, Angew. Chem. 2008, 120, 3144-3164;
14. Angew. Chem. Int. Ed. 2008, 47, 3100-3120.
15. For palladium-catalyzed decarboxylative Heck-Mizoroki olefination reactions, see: a) A. G. Myers, D. Tanaka, M. R. Mannion, J. Am. Chem. Soc. 2002, 124, 11250-11251;
16. b) D. Tanaka, A. G. Myers, Org. Lett. 2004, 6, 433-436;
17. c) D. Tanaka, S. P. Romeril, A. G. Myers, J. Am. Chem. Soc. 2005, 127, 1032310333;
18. d) A. Maehara, H. Tsurugi, T. Satoh, M. Miura, Org. Lett. 2008, 10, 1159-1162.
19. For palladium-catalyzed decarboxylative biaryl synthesis, see: a) L. J. Gooßen, G. Deng, L. M. Levy, Science 2006, 313, 662664;
20. b) L. J. Gooßen, N. Rodríguez, M. Bettina, C. Linder, G. Deng, L. M. Levy, J. Am. Chem. Soc. 2007, 129, 4824-4833;
21. c) L. J. Gooßen, F. Rudolphi, C. Oppel, N. Rodríguez, Angew. Chem. 2008, 120, 3085-3088;
22. Angew. Chem. Int. Ed. 2008, 47, 3043-3045;
23. d) L.J. Gooßen, B. Zimmermann, T. Knauber, Angew. Chem. 2008, 120, 7211-7214;
24. Angew. Chem. Int. Ed. 2008, 47, 7103-7106;
25. e) L. J. Gooßen, N. Rodríguez, C. Linder, J. Am. Chem. Soc. 2008, 130, 15248-15249;
26. f) P. Forgione, M.-C. Brochu, M. St-Onge, K. H. Thesen, M. D. Bailey, F. Bilodeau, J. Am. Chem. Soc. 2006, 128, 11350-11351;
27. g) J.-M. Becht, C. D. Catala, C. Le Drian, A. Wagner, Org. Lett. 2007, 9, 781-784;
28. h) M. Nakano, H. Tsurugi, T. Satoh, M. Miura, Org. Lett. 2008, 10, 1851-1854;
29. i) J.-M. Becht, C. Le Drian, Org. Lett. 2008, 10, 3161-3164;
30. j) A. Voutchkova, A. Coplin, N. E. Leadbeater, R. H. Crabtree, Chem. Commun. 2008, 6312-6314.
31. For copper- and palladium-catalyzed reductive decarboxylation, see: a) L. J. Gooßen, W. R. Thiel, N. Rodríguez, C. Linder, B. Melzer, Adv. Synth. Catal. 2007, 349, 2241-2246;
32. b) J. S. Dickstein, C. A. Mulrooney, E. M. O'Brien, B. J. Morgan, M. C. Kozlowski, Org. Lett. 2007, 9, 2441-2444.
33. For rhodium- and iridium-catalyzed decarboxylative alkyne insertion, see: K. Ueura, T. Satoh, M. Miura, J. Org. Chem. 2007, 72, 5362-5367.
34. For recent examples of palladium-catalyzed decarboxylative allylation and the decarboxylative protonation of activated allylic esters, see: a) D. E. White, I. C. Stewart, R. H. Grubbs, B. M. Stoltz, J. Am. Chem. Soc. 2008, 130, 810-811;
35. b) C. Wang, J. A. Tunge, J. Am. Chem. Soc. 2008, 130, 8118-8119.
36. a) A. D. English, T. Herskovitz, J. Am. Chem. Soc. 1977, 99,1648-1649;
37. b) M. Aresta, A. Dibenedetto, P. Michelangelo, E. Quaranta, I. Tommasi, J. Organomet. Chem. 2000, 605,143-150.
38. a) K. Ukai, M. Aoki, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2006, 128, 8706-8707;
39. b) C. S. Yeung, V. M. Dong, J. Am. Chem. Soc. 2008, 130, 1816-1811.
40. For a recent example, see: H.A. Chiong, Q.-N. Pham, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 9879-9884.
41. For the rhodium-catalyzed conjugate addition of carboxylic acids and alcohols as oxygen-based nucleophiles, see: M. V. Farnworth, M.J. Cross, J. Louie, Tetrahedron Lett. 2004, 45, 7441-7443.
42. G. Zou, J. Guo, Z. Wang, W. Huang, J. Tang, Dalton Trans. 2007, 3055-3064.
43. 3- ligated Rh and Ir perfluorinated benzoates, see: a) G. B. Deacon, S. J. Faulks, J. M. Miller, Transition Met. Chem. 1980, 5, 305-313;
44. b) G. B. Deacon, S. J. Faulks, J. Organomet. Chem. 1992, 437, 239-249.
45. K. Mueller, C. Faeh, F. Diederich, Science 2007, 317,1881-1886.
46. V. V. Grushin, V. F. Kuznetsov, C. Bensimon, H. Alper, Organometallics 1995, 14, 3927-3932; cod = 1,5-cyclooctadiene.
47. 2 release, and subsequent pyridine coordination to stabilize the final product.
48. For examples of relevant reported structures, see: a) H. Werner, M. Schäfer, O. Nürnberg, J.Wolf, Chem. Ber. 1994, 127, 27-38;
49. b) C. Krug, J. F. Hartwig, J. Am. Chem. Soc. 2004, 126, 26942695. CCDC 704653 (1) and 704654 (6) contain 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.
50. [l9b] which suggests the existence of an additional, ligand-dependent thermodynamic driving force for decarboxylation.
51. 2 scavenger to promote decarboxylation. Additionally, the formation of sodium benzoate may promote the decarboxylation process as suggested in Ref. [6e].
52. (R,R)-Diop = (4.R,5.R)-(-)-4,5-bis(diphenylphosphanylmethyl)2,2- dimethyl-l,3-dioxolane.
53. [7a]