Palladium(II)-Catalyzed Oxidative Difunctionalization of Alkenes: Bond Forming at a High-Valent Palladium Center

Accounts of Chemical Research

Volumn 49, Issue 11, 2016, Pages 2413-2423

  Yin, Guoyin ^a   Mu, Xin ^a   Liu, Guosheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84995767461     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.6b00328     Document Type: Article

References (67)

1. Togni, A., Grutzmacher, H., Eds. Catalytic Heterofunctionalization; Wiley-VCH: Weinheim, 2001.
2. Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: recent development and trends Angew. Chem., Int. Ed. 2004, 43, 3368-3398 10.1002/anie.200300616
3. Bäckvall, J. E. Palladium in some selective oxidation reactions Acc. Chem. Res. 1983, 16, 335-342 10.1021/ar00093a004
4. Schultz, D. M.; Wolfe, J. P. Recent Developments in Palladium-Catalyzed Alkene Aminoarylation Reactions Synthesis 2012, 44, 351-361 10.1055/s-0031-1289668
5. Nigishi, E. J. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-VCH: Weinheim, 2002, Vol. 2.
6. Filler, R.; Kobayashi, Y. Biomedicinal Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1982.
7. Welch, J. T.; Eswarakrishman, S., Eds. Fluorine in Bioorganic Chemistry; Wiley: New York, 1991.
8. Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New York, 1994.
9. Canty, A. J. Organopalladium and platinum chemistry in oxidising milieu as models for organic synthesis involving the higher oxidation states of palladium Dalton. Trans. 2009, 47, 10409-10417 10.1039/b914080h
10. Canty, A. J. Development of organopalladium(IV) chemistry: fundamental aspects and systems for studies of mechanism in organometallic chemistry and catalysis Acc. Chem. Res. 1992, 25, 83-90 10.1021/ar00014a005
11. Fekl, U.; Kaminsky, W.; Goldberg, K. I. A stable Five-Coordinate Platinum(IV) Alkyl Complex J. Am. Chem. Soc. 2001, 123, 6423-6424 10.1021/ja0156690
12. Catellani, E.; Motti, N.; Della Ca', N. Catalytic Sequential Reactions Involving Palladacycle-Directed Aryl Coupling Steps Acc. Chem. Res. 2008, 41, 1512-1522 10.1021/ar800040u
13. Neufeldt, S. R.; Sanford, M. S. Controlling Site Selectivity in Palladium-Catalyzed C-H Bond Functionalization Acc. Chem. Res. 2012, 45, 936-946 10.1021/ar300014f
14. Giri, R.; Liang, J.; Lei, J.-G.; Li, J.-J.; Wang, D.-H.; Chen, X.; Naggar, I. C.; Guo, C.; Foxman, B. M.; Yu, J.-Q. Pd-Catalyzed Stereoselective Oxidation of Methyl Groups by Inexpensive Oxidants under Mild Conditions: A Dual Role for Carboxylic Anhydrides in Catalytic C-H Bond Oxidation Angew. Chem., Int. Ed. 2005, 44, 7420-7424 10.1002/anie.200502767
15. Daugulis, O.; Do, H.-Q.; Shabashov, D. Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds Acc. Chem. Res. 2009, 42, 1074-1086 10.1021/ar9000058
16. Daugulis, O.; Roane, J.; Tran, L. D. Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon-Hydrogen Bonds Acc. Chem. Res. 2015, 48, 1053-1064 10.1021/ar5004626
17. Powers, D. C.; Ritter, T. Bimetallic Synergy in Oxidative Palladium Catalysis Acc. Chem. Res. 2012, 45, 840-850 10.1021/ar2001974
18. Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Emergence of Palladium(IV) Chemistry in Synthesis and Catalysis Chem. Rev. 2010, 110, 824-889 10.1021/cr9003242
19. Hickman, A. J.; Sanford, M. S. High-valent organometallic copper and palladium in catalysis Nature 2012, 484, 177-185 10.1038/nature11008
20. Muñiz, K. High-Oxidation-State Palladium Catalysis: New Reactivity for Organic Synthesis Angew. Chem., Int. Ed. 2009, 48, 9412-9423 10.1002/anie.200903671
21. + Oxidant Enable Selective Reductive Elimination from High-Valent Metal Centers in Catalysis Angew. Chem., Int. Ed. 2011, 50, 1478-1491 10.1002/anie.201005142
22. Alexanian, E. J.; Lee, C.; Sorensen, E. J. Palladium-Catalyzed Ring-Forming Aminoacetoxylation of Alkenes J. Am. Chem. Soc. 2005, 127, 7690-7691 10.1021/ja051406k
23. Streuff, J.; Hövelmann, C. H.; Nieger, M.; Muñiz, K. Palladium(II)-Catalyzed Intramolecular Diamination of Unfunctionalized Alkenes J. Am. Chem. Soc. 2005, 127, 14586-14587 10.1021/ja055190y
24. Muñiz, K.; Hövelmann, C. H.; Streuff, J. Oxidative Diamination of Alkenes with Ureas as Nitrogen Sources: Mechanistic Pathways in the Presence of a High Oxidation State Palladium Catalyst J. Am. Chem. Soc. 2008, 130, 763-773 10.1021/ja075041a
25. Muñiz, K. Advancing Palladium-Catalyzed C-N Bond Formation: Bisindoline Construction from Successive Amide Transfer to Internal Alkenes J. Am. Chem. Soc. 2007, 129, 14542-14543 10.1021/ja075655f
26. Iglesias, á.; Pérez, E. G.; Muñiz, K. An Intermolecular Palladium-Catalyzed Diamination of Unactivated Alkenes Angew. Chem., Int. Ed. 2010, 49, 8109 10.1002/anie.201003653
27. Martínez, C.; Muñiz, K. Palladium-Catalyzed Vicinal Difunctionalization of Internal Alkenes: Diastereoselective Synthesis of Diamines Angew. Chem., Int. Ed. 2012, 51, 7031-7034 10.1002/anie.201201719
28. N2 C-O Bond Formation J. Am. Chem. Soc. 2006, 128, 7179-7181 10.1021/ja061706h
29. 2 on Aminopalladation Stereoselectivity J. Org. Chem. 2013, 78, 6309-6315 10.1021/jo400671q
30. IV-Catalyzed Aminooxygenation of Alkenes Angew. Chem., Int. Ed. 2007, 46, 5737-5740 10.1002/anie.200701454
31. Kalyani, D.; Sanford, M. S. Oxidatively Intercepting Heck Intermediates: Pd-Catalyzed 1,2- and 1,1-Arylhalogenation of Alkenes J. Am. Chem. Soc. 2008, 130, 2150-2151 10.1021/ja0782798
32. Rosewall, C. F.; Sibbald, P. A.; Liskin, D. V.; Michael, F. E. Palladium-Catalyzed Carboamination of Alkenes Promoted by N-Fluorobenzenesulfonimide via C-H Activation of Arenes J. Am. Chem. Soc. 2009, 131, 9488-9489 10.1021/ja9031659
33. Sibbald, P. A.; Rosewall, C. F.; Swartz, R. D.; Michael, F. E. Mechanism of N-Fluorobenzenesulfonimide Promoted Diamination and Carboamination Reactions: Divergent Reactivity of a Pd(IV) Species J. Am. Chem. Soc. 2009, 131, 15945-15951 10.1021/ja906915w
34. Jacobson, O.; Kiesewetter, D. O.; Chen, X. Fluorine-18 Radiochemistry, Labeling Strategies and Synthetic Routes Bioconjugate Chem. 2015, 26, 1-18 10.1021/bc500475e
35. Grushin, V. V. The Organometallic Fluorine Chemistry of Palladium and Rhodium: Studies toward Aromatic Fluorination Acc. Chem. Res. 2010, 43, 160-171 10.1021/ar9001763
36. Hull, K. L.; Anani, W. Q.; Sanford, M. S. Palladium-Catalyzed Fluorination of Carbon-Hydrogen Bonds J. Am. Chem. Soc. 2006, 128, 7134-7135 10.1021/ja061943k
37. 2O-Catalyzed ortho-Fluorination Using NMP as a Promoter J. Am. Chem. Soc. 2009, 131, 7520-7521 10.1021/ja901352k
38. Ball, N. D.; Sanford, M. S. Synthesis and Reactivity of a Mono-σ-Aryl Palladium(IV) Fluoride Complex J. Am. Chem. Soc. 2009, 131, 3796-3797 10.1021/ja8054595
39. Furuya, T.; Ritter, T. Carbon-Fluorine Reductive Elimination from a High-Valent Palladium Fluoride J. Am. Chem. Soc. 2008, 130, 10060-10061 10.1021/ja803187x
40. 2, Cl, Br) J. Am. Chem. Soc. 2010, 132, 14400-14402 10.1021/ja107185w
41. Yin, G.; Liu, G. Palladium-Catalyzed Oxidative Cyclization of Enynes with Hydrogen Peroxide as the Oxidant Angew. Chem., Int. Ed. 2008, 47, 5442-5445 10.1002/anie.200801438
42. Wu, T.; Yin, G.; Liu, G. Palladium-Catalyzed Intramolecular Aminofluorination of Unactivated Alkenes J. Am. Chem. Soc. 2009, 131, 16354-16355 10.1021/ja9076588
43. Cheng, J.; Chen, P.; Liu, G. Pd-Catalyzed Intramolecular Aminofluorination of allylic Sulfamides Chin. J. Catal. 2015, 36, 40-47 10.1016/S1872-2067(14)60164-9
44. Wu, T.; Cheng, J.; Chen, P.; Liu, G. Regioselective palladium-catalyzed intramolecular oxidative aminofluorination of unactivated alkenes Chem. Commun. 2013, 49, 8707-8709 10.1039/c3cc44711a
45. Wu, L.; Chen, P.; Liu, G. Pd(II)-Catalyzed Aminofluorination of Alkenes in Total Synthesis 6-(R)-Fluoroswainsonine and 5-(R)-Fluorofebrifugine Org. Lett. 2016, 18, 960-963 10.1021/acs.orglett.6b00030
46. Zhu, H.; Liu, G. Pallaium-catalyzed oxidative aminofluorination of styrenes Acta. Chimica. Sinica. 2012, 70, 2404-2407 10.6023/A12100835
47. McMurtrey, K. B.; Racowski, J. M.; Sanford, M. S. Pd-Catalyzed C-H Fluorination with Nucleophilic Fluoride Org. Lett. 2012, 14, 4094-4097 10.1021/ol301739f
48. Chen, S.; Wu, T.; Liu, G.; Zhen, X. Highly Selective Palladium-Catalyzed Intramolecular Aminonitroxylation of Alkenes Synlett 2011, 2011, 891-894 10.1055/s-0030-1259701
49. Mu, X.; Chen, S.; Zhen, X.; Liu, G. Palladium-Catalyzed Oxidative Trifluoromethylation of Indoles at Room Temperature Chem.-Eur. J. 2011, 17, 6039-6042 10.1002/chem.201100283
50. Mu, X.; Wu, T.; Wang, H.-y.; Guo, Y.-l.; Liu, G. Palladium-Catalyzed Oxidative Aryltrifluoromethylation of Activated Alkenes at Room Temperature J. Am. Chem. Soc. 2012, 134, 878-881 10.1021/ja210614y
51. Wang, X.; Truesdale, L.; Yu, J.-Q. Pd(II)-Catalyzed ortho-Trifluoromethylation of Arenes Using TFA as a Promoter J. Am. Chem. Soc. 2010, 132, 3648-3649 10.1021/ja909522s
52. +": Formation and Reactivity of a Catalytically Competent Monomeric Pd(IV) Aquo Complex J. Am. Chem. Soc. 2010, 132, 14682-14687 10.1021/ja107780w
53. Zhang, C.-P.; Vicic, D. A. Oxygen-Bound Trifluoromethoxide Complexes of Copper and Gold Organometallics 2012, 31, 7812-7815 10.1021/om3002747
54. Chen, C.; Chen, P.; Liu, G. Palladium-Catalyzed Intramolecular Aminotrifluoromethoxylation of Alkenes J. Am. Chem. Soc. 2015, 137, 15648-15651 10.1021/jacs.5b10971
55. Racowski, J. M.; Gary, J. B.; Sanford, M. S. Carbon (sp3) Fluorine Bond-Forming Reductive Elimination from Palladium(IV) Complexes Angew. Chem., Int. Ed. 2012, 51, 3414-3417 10.1002/anie.201107816
56. Khusnutdinova, J. R.; Rath, N. P.; Mirica, L. M. The Aerobic Oxidation of a Pd(II) Dimethyl Complex Leads to Selective Ethane Elimination from a Pd(III) Intermediate J. Am. Chem. Soc. 2012, 134, 2414-2422 10.1021/ja210841f
57. 2 Acc. Chem. Res. 2012, 45, 803-813 10.1021/ar200191k
58. Roussel, M.; Mimoun, H. Palladium-catalyzed oxidation of terminal olefins to methyl ketones by hydrogen peroxide J. Org. Chem. 1980, 45, 5387-5390 10.1021/jo01314a042
59. Yin, G.; Wu, T.; Liu, G. Highly Selective Palladium-Catalyzed Intramolecular Chloroamination of Unactivated Alkenes by Using Hydrogen Peroxide as an Oxidant Chem.-Eur. J. 2012, 18, 451-455 10.1002/chem.201102776
60. Yin, G. Palladium-catalyzed Oxidative Transformation of Alkenes, Ph.D. Thesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, June 2011.
61. Zhang, Q.; Lu, X.; Han, X. Palladium(II)-Catalyzed Asymmetric Cyclization of (Z)-4′-Acetoxy-2′-butenyl 2-Alkynoates. Role of Nitrogen-Containing Ligands in Palladium(II)-Mediated Reactions J. Org. Chem. 2001, 66, 7676-7684 10.1021/jo0105181
62. Zhu, H.; Chen, P.; Liu, G. Palladium-Catalyzed Intramolecular Aminoacetoxylation of Unactivated Alkenes with Hydrogen Peroxide as Oxidant Org. Lett. 2015, 17, 1485-1488 10.1021/acs.orglett.5b00373
63. Kalyani, D.; Satterfield, A. D.; Sanford, M. S. Palladium-Catalyzed Oxidative Arylhalogenation of Alkenes: Synthetic Scope and Mechanistic Insights J. Am. Chem. Soc. 2010, 132, 8419-8427 10.1021/ja101851v
64. Zhu, H.; Chen, P.; Liu, G. Pd-Catalyzed Intramolecular Aminohydroxylation of Alkenes with Hydrogen Peroxide as Oxidant and Water as Nucleophile J. Am. Chem. Soc. 2014, 136, 1766-1769 10.1021/ja412023b
65. 18OH, OH, OMe; L = di(2-pyridyl)methane sulfonate) Organometallics 2007, 26, 3466-3483 10.1021/om070165h
66. White, P. B.; Stahl, S. S. Reversible Alkene Insertion into the Pd-N Bond of Pd(II)-Sulfonamidates and Implications for Catalytic Amidation Reactions J. Am. Chem. Soc. 2011, 133, 18594-18597 10.1021/ja208560h
67. sp3-F Reductive Eliminations Feasible Organometallics 2011, 30, 3926-3929 10.1021/om200515f