Tuning Reactivity and Selectivity in Hydrogen Atom Transfer from Aliphatic C-H Bonds to Alkoxyl Radicals: Role of Structural and Medium Effects

Accounts of Chemical Research

Volumn 48, Issue 11, 2015, Pages 2895-2903

  Salamone, Michela ^a   Bietti, Massimo ^a  

^a UNIVERSITY OF ROME TOR VERGATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84947236214     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00348     Document Type: Article

References (50)

1. Mayer, J. M. Understanding Hydrogen Atom Transfer: From Bond Strengths to Marcus Theory Acc. Chem. Res. 2011, 44, 36-46 10.1021/ar100093z
2. Saouma, C. T.; Mayer, J. M. Do Spin State and Spin Density Affect Hydrogen Atom Transfer Reactivity? Chem. Sci. 2014, 5, 21-31 10.1039/C3SC52664J
3. Lai, W.; Li, C.; Chen, H.; Shaik, S. Hydrogen-Abstraction Reactivity Patterns from A to Y: The Valence Bond Way Angew. Chem., Int. Ed. 2012, 51, 5556-5578 10.1002/anie.201108398
4. Dietl, N.; Schlangen, M.; Schwarz, H. Thermal Hydrogen-Atom Transfer from Methane: The Role of Radicals and Spin States in Oxo-Cluster Chemistry Angew. Chem., Int. Ed. 2012, 51, 5544-5555 10.1002/anie.201108363
5. Roberts, B. P. Polarity-Reversal Catalysis of Hydrogen-Atom Abstraction Reactions: Concepts and Applications in Organic Chemistry Chem. Soc. Rev. 1999, 28, 25-35 10.1039/a804291h
6. Valgimigli, L.; Pratt, D. A. Maximizing the Reactivity of Phenolic and Aminic Radical-Trapping Antioxidants: Just Add Nitrogen! Acc. Chem. Res. 2015, 48, 966-975 10.1021/acs.accounts.5b00035
7. Ingold, K. U.; Pratt, D. A. Advances in Radical-Trapping Antioxidant Chemistry in the 21st Century: A Kinetics and Mechanisms Perspective Chem. Rev. 2014, 114, 9022-9046 10.1021/cr500226n
8. Litwinienko, G.; Ingold, K. U. Solvent Effects on the Rates and Mechanisms of Reaction of Phenols with Free Radicals Acc. Chem. Res. 2007, 40, 222-230 10.1021/ar0682029
9. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 4 th ed.; Oxford University Press: Oxford, 2007.
10. Yin, H.; Xu, L.; Porter, N. A. Free Radical Lipid Peroxidation: Mechanisms and Analysis Chem. Rev. 2011, 111, 5944-5972 10.1021/cr200084z
11. Broderick, J. B.; Duffus, B. R.; Duschene, K. S.; Shepard, E. M. Radical S-Adenosylmethionine Enzymes Chem. Rev. 2014, 114, 4229-4317 10.1021/cr4004709
12. Minnihan, E. C.; Nocera, D. G.; Stubbe, J. Reversible, Long-Range Radical Transfer in E. coli Class Ia Ribonucleotide Reductase Acc. Chem. Res. 2013, 46, 2524-2535 10.1021/ar4000407
13. Shaik, S.; Lai, W.; Chen, H.; Wang, Y. The Valence Bond Way: Reactivity Patterns of Cytochrome P450 Enzymes and Synthetic Analogs Acc. Chem. Res. 2010, 43, 1154-1165 10.1021/ar100038u
14. Liu, W.; Groves, J. T. Manganese Catalyzed C-H Halogenation Acc. Chem. Res. 2015, 48, 1727-1735 10.1021/acs.accounts.5b00062
15. Nam, W.; Lee, Y.-M.; Fukuzumi, S. Tuning Reactivity and Mechanism in Oxidation Reactions by Mononuclear Nonheme Iron(IV)-Oxo Complexes Acc. Chem. Res. 2014, 47, 1146-1154 10.1021/ar400258p
16. Atkinson, R.; Arey, J. Atmospheric Degradation of Volatile Organic Compounds Chem. Rev. 2003, 103, 4605-4638 10.1021/cr0206420
17. White, M. C. Adding Aliphatic C-H Bond Oxidations to Synthesis Science 2012, 335, 807-809 10.1126/science.1207661
18. Newhouse, T.; Baran, P. S. If C-H Bonds Could Talk: Selective C-H Bond Oxidation Angew. Chem., Int. Ed. 2011, 50, 3362-3374 10.1002/anie.201006368
19. Lewis, J. C.; Coelho, P. S.; Arnold, F. H. Enzymatic Functionalization of Carbon-Hydrogen Bonds Chem. Soc. Rev. 2011, 40, 2003-2021 10.1039/C0CS00067A
20. Salamone, M.; Bietti, M. Reaction Pathways of Alkoxyl Radicals. The Role of Solvent Effects on C-C Bond Fragmentation and Hydrogen Atom Transfer Reactions Synlett 2014, 25, 1803-1816 10.1055/s-0033-1341280
21. Baciocchi, E.; Bietti, M.; Salamone, M.; Steenken, S. Spectral Properties and Absolute Rate Constants for β-Scission of Ring Substituted Cumyloxyl Radicals. A Laser Flash Photolysis Study J. Org. Chem. 2002, 67, 2266-2270 10.1021/jo0163041
22. Avila, D. V.; Ingold, K. U.; Di Nardo, A. A.; Zerbetto, F.; Zgierski, M. Z.; Lusztyk, J. Electronic Absorption Spectra of Some Alkoxyl Radicals. An Experimental and Theoretical Study J. Am. Chem. Soc. 1995, 117, 2711-2718 10.1021/ja00115a005
23. Walling, C. Some Aspects of the Chemistry of Alkoxy Radicals Pure Appl. Chem. 1967, 15, 69-80 10.1351/pac196715010069
24. Finn, M.; Friedline, R.; Suleman, N. K.; Wohl, C. J.; Tanko, J. M. Chemistry of the t-Butoxyl Radical: Evidence that Most Hydrogen Abstractions from Carbon are Entropy-Controlled J. Am. Chem. Soc. 2004, 126, 7578-7584 10.1021/ja0493493
25. Salamone, M.; DiLabio, G. A.; Bietti, M. Hydrogen Atom Abstraction Selectivity in the Reactions of Alkylamines with the Benzyloxyl and Cumyloxyl Radicals. The Importance of Structure and of Substrate-Radical Hydrogen Bonding J. Am. Chem. Soc. 2011, 133, 16625-16634 10.1021/ja206890y
26. Pischel, U.; Nau, W. M. Switch-Over in Photochemical Reaction Mechanism from Hydrogen Abstraction to Exciplex-Induced Quenching: Interaction of Triplet-Excited versus Singlet-Excited Acetone versus Cumyloxyl Radicals with Amines J. Am. Chem. Soc. 2001, 123, 9727-9737 10.1021/ja011212e
27. Griller, D.; Howard, J. A.; Marriott, P. R.; Scaiano, J. C. Absolute Rate Constants for the Reactions of tert-Butoxyl, tert-Butylperoxyl, and Benzophenone Triplet with Amines: The Importance of a Stereoelectronic Effect J. Am. Chem. Soc. 1981, 103, 619-623 10.1021/ja00393a020
28. Bietti, M.; Martella, R.; Salamone, M. Understanding Kinetic Solvent Effects on Hydrogen Abstraction Reactions from Carbon by the Cumyloxyl Radical Org. Lett. 2011, 13, 6110-6113 10.1021/ol202561z
29. Salamone, M.; DiLabio, G. A.; Bietti, M. Reactions of the Cumyloxyl and Benzyloxyl Radicals with Strong Hydrogen Bond Acceptors. Large Enhancements in Hydrogen Abstraction Reactivity Determined by Substrate/Radical Hydrogen Bonding J. Org. Chem. 2012, 77, 10479-10487 10.1021/jo3019889
30. Luo, Y.-R. Comprehensive Handbook of Chemical Bond Energies; CRC Press: Boca Raton, FL, 2007.
31. Salamone, M.; Basili, F.; Bietti, M. Reactivity and Selectivity Patterns in Hydrogen Atom Transfer from Amino Acid C-H Bonds to the Cumyloxyl Radical. Polar Effects as a Rationale for the Preferential Reaction at Proline Residues J. Org. Chem. 2015, 80, 3643-3650 10.1021/acs.joc.5b00549
32. Salamone, M.; Martella, R.; Bietti, M. Hydrogen Abstraction from Cyclic Amines by the Cumyloxyl and Benzyloxyl Radicals. The Role of Stereoelectronic Effects and of Substrate/Radical Hydrogen Bonding J. Org. Chem. 2012, 77, 8556-8561 10.1021/jo3015352
33. Malatesta, V.; Scaiano, J. C. Absolute Rate Constants for the Reactions of tert-Butoxyl with Ethers: Importance of the Stereoelectronic Effect J. Org. Chem. 1982, 47, 1455-1459 10.1021/jo00347a015
34. Salamone, M.; Milan, M.; DiLabio, G. A.; Bietti, M. Absolute Rate Constants for Hydrogen Atom Transfer from Tertiary Amides to the Cumyloxyl Radical. Evaluating the Role of Stereoelectronic Effects J. Org. Chem. 2014, 79, 7179-7184 10.1021/jo5013459
35. Salamone, M.; Ortega, V. B.; Bietti, M. Enhanced Reactivity in Hydrogen Atom Transfer from Tertiary Sites of Cyclohexanes and Decalins via Strain Release. Equatorial C-H Activation vs Axial C-H Deactivation J. Org. Chem. 2015, 80, 4710-4715 10.1021/acs.joc.5b00636
36. Amorati, R.; Valgimigli, L. Modulation of the Antioxidant Activity of Phenols by Non-Covalent Interactions Org. Biomol. Chem. 2012, 10, 4147-4158 10.1039/c2ob25174d
37. Bietti, M.; Salamone, M.; DiLabio, G. A.; Jockusch, S.; Turro, N. J. Kinetic Solvent Effects on Hydrogen Abstraction from Phenol by the Cumyloxyl Radical. Towards an Understanding of the Role of Protic Solvents J. Org. Chem. 2012, 77, 1267-1272 10.1021/jo201454c
38. Bietti, M.; Salamone, M. Kinetic Solvent Effects on Hydrogen Abstraction Reactions from Carbon by the Cumyloxyl Radical. The Role of Hydrogen Bonding Org. Lett. 2010, 12, 3654-3657 10.1021/ol101448e
39. Avila, D. V.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. Solvent Effects on the Competitive β-Scission and Hydrogen Atom Abstraction Reactions of the Cumyloxyl Radical. Resolution of a Long Standing Problem J. Am. Chem. Soc. 1993, 115, 466-470 10.1021/ja00055a015
40. Salamone, M.; Giammarioli, I.; Bietti, M. Kinetic Solvent Effects on Hydrogen Abstraction Reactions from Carbon by the Cumyloxyl Radical. The Importance of Solvent Hydrogen Bond Interactions with the Substrate and the Abstracting Radical J. Org. Chem. 2011, 76, 4645-4651 10.1021/jo200660d
41. Mitroka, S.; Zimmeck, S.; Troya, D.; Tanko, J. M. How Solvent Modulates Hydroxyl Radical Reactivity in Hydrogen Atom Abstractions J. Am. Chem. Soc. 2010, 132, 2907-2913 10.1021/ja903856t
42. Salamone, M.; Mangiacapra, L.; Bietti, M. Kinetic Solvent Effects on the Reactions of the Cumyloxyl Radical with Tertiary Amides. Control Over the Hydrogen Atom Transfer Reactivity and Selectivity Through Solvent Polarity and Hydrogen Bonding J. Org. Chem. 2015, 80, 1149-1154 10.1021/jo5026767
43. Reichardt, C.; Welton, T. Solvents and Solvent Effects in Organic Chemistry, 4 th ed.; Wiley-VCH: Weinheim, 2010.
44. Salamone, M.; Milan, M.; DiLabio, G. A.; Bietti, M. Reactions of the Cumyloxyl and Benzyloxyl Radicals with Tertiary Amides. Hydrogen Abstraction Selectivity and the Role of Specific Substrate-Radical Hydrogen Bonding J. Org. Chem. 2013, 78, 5909-5917 10.1021/jo400535u
45. Salamone, M.; Giammarioli, I.; Bietti, M. Tuning Hydrogen Atom Abstraction from the Aliphatic C-H Bonds of Basic Substrates by Protonation. Control Over Selectivity by C-H Deactivation Chemical Science 2013, 4, 3255-3262 10.1039/c3sc51058a
46. Milan, M.; Salamone, M.; Bietti, M. Hydrogen Atom Transfer from 1,n-Alkanediamines to the Cumyloxyl Radical. Modulating C-H Deactivation Through Acid-Base Interactions and Solvent Effects J. Org. Chem. 2014, 79, 5710-5716 10.1021/jo5008493
47. Salamone, M.; Mangiacapra, L.; DiLabio, G. A.; Bietti, M. The Effect of Metal Ions on the Reactions of the Cumyloxyl Radical with Hydrogen Atom Donors. Fine Control on Hydrogen Abstraction Reactivity Determined by Lewis Acid-Base Interactions J. Am. Chem. Soc. 2013, 135, 415-423 10.1021/ja309579t
48. Salamone, M.; Carboni, G.; Mangiacapra, L.; Bietti, M. Binding to Redox-Inactive Alkali and Alkaline Earth Metal Ions Strongly Deactivates the C-H Bonds of Tertiary Amides Toward Hydrogen Atom Transfer to Reactive Oxygen Centered Radicals J. Org. Chem. 2015, 80, 9214-9223 10.1021/acs.joc.5b01661
49. Nova, A.; Balcells, D. Does the Metal Protect the Ancillary Ligands? C-H Strengthening and Deactivation in Amines and Phosphines Upon Metal-Binding Chem. Commun. 2014, 50, 614-616 10.1039/C3CC47686C
50. Salamone, M.; Amorati, R.; Menichetti, S.; Viglianisi, C.; Bietti, M. Structural and Medium Effects on the Reactions of the Cumyloxyl Radical with Intramolecular Hydrogen Bonded Phenols. The Interplay Between Hydrogen-Bonding and Acid-Base Interactions on the Hydrogen Atom Transfer Reactivity and Selectivity J. Org. Chem. 2014, 79, 6196-6205 10.1021/jo5009367