Synthetic Organic Methodology

Organofluorine Methodology
Decarboxylative and Deoxygenative Fluoroalkylation
Fluorinated Alkenes
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59. Insights into Deoxytrifluoromethylation /Aromatization to Access Highly Substituted Trifluoromethyl Arenes
59. Insights into Deoxytrifluoromethylation /Aromatization to Access Highly Substituted Trifluoromethyl Arenes

Bhattarai, P.; Abd El-Gaber, M. K.; Koley, S.K.; Altman, R. A.*

J. Org. Chem. 2025, 90, 14291–14303.

58. Unified Enantioselective Synthesis of 5-Phenylmorphans and cis-Octahydroisoquinolines
58. Unified Enantioselective Synthesis of 5-Phenylmorphans and cis-Octahydroisoquinolines

Mahgoub, A.; Khamrai, J.; Festus, O.; Altman, R. A.*

Org. Lett., 2025, 27, 8941–8945.

57. NBS-Promoted Synthesis of Maleimides by Oxidative Dearomatization of Pyrroles: Mechanistic Investigations Using Online MS in Real-Time
57. NBS-Promoted Synthesis of Maleimides by Oxidative Dearomatization of Pyrroles: Mechanistic Investigations Using Online MS in Real-Time

Kumar, A.; Mishra, P. K.; Nandy, A.; Altman, R. A.; Banerjee, S.; Verma, A. K.*

Org. Lett., 2025, 27, 7810–7815.

55. A Deoxyfluoroalkylation-Aromatization Strategy to Access Fluoroalkyl Arenes
55. A Deoxyfluoroalkylation-Aromatization Strategy to Access Fluoroalkyl Arenes

Bhattarai, P.; Koley, S. K.; Goel, K.; Altman, R. A.*

Chem. Commun. 2025, 61, 2524–2527.

54. Synthesis of 4-(2,2-Difluorovinyl)benzonitrile through a Wittig-type Olefination of 4-Formylbenzonitrile
54. Synthesis of 4-(2,2-Difluorovinyl)benzonitrile through a Wittig-type Olefination of 4-Formylbenzonitrile

Intelli. A. J.; Sorrentino, J. P.; Altman, R. A.*

Org. Synth. 2024, 101, 542.

51. Palladium and Copper Co-Catalyzed Chloro-Arylation of gem-Difluorostyrenes – Use of a Nitrite Additive to Suppress β-F Elimination
51. Palladium and Copper Co-Catalyzed Chloro-Arylation of gem-Difluorostyrenes – Use of a Nitrite Additive to Suppress β-F Elimination

Intelli, A. J.; Wayment, C. Z.; Lee, R. T.; Yuan, K.; Altman, R. A.*

Chem. Sci. 2024, 15, 17571–17578.

50. Deoxytrifluoromethylation/Aromatization of Cyclohexan(en)ones to Access Highly Substituted Trifluoromethylarenes
50. Deoxytrifluoromethylation/Aromatization of Cyclohexan(en)ones to Access Highly Substituted Trifluoromethylarenes

Bhattarai, P.; Abd El-Gaber, M. K.; Koley, S. K.; Altman, R. A.* 

Nat. Commun. 2024, 15, 7882.

49. Peroxide-Initiated Hydrophosphination of gem-Difluoroalkenes
49. Peroxide-Initiated Hydrophosphination of gem-Difluoroalkenes

Intelli, A. J.; Lee, R. T.; Altman, R. A.*

J. Org. Chem. 2023, 88, 14012–14021.

48. Palladium-Catalyzed Dearomatization of Benzothiophenes: Isolation and Functionalization of a Discrete Dearomatized Intermediate
48. Palladium-Catalyzed Dearomatization of Benzothiophenes: Isolation and Functionalization of a Discrete Dearomatized Intermediate

Intelli, A. J.; Pal, M.; Selvaraju, M.; Altman, R. A.*

Synthesis 2023, 55, 3568–3574.

47. A Diselenide Additive Enables Photocatalytic Hydroalkoxylation of gem-Difluoroalkenes
47. A Diselenide Additive Enables Photocatalytic Hydroalkoxylation of gem-Difluoroalkenes

Herrick, R. M.; Abd El-Gaber, M. K.; Rodriguez, L. G. C.; Altman, R. A.*

Chem. Commun. 2023, 59, 5623–5626.

46. Photocatalytic Hydrothiolation of gem-Difluoroalkenes
46. Photocatalytic Hydrothiolation of gem-Difluoroalkenes

Sorrentino, J. P.; Herrick, R. M.; Abd El-Gaber, M. K.; Abdelazem, A. Z.; Altman, R. A.*

J. Org. Chem. 2022, 87, 16676–16690.

45. Cu(II)-Catalyzed Oxidation of gem-Difluoroalkenes Generate α,α-Difluorinated-α-Phenoxyketones
45. Cu(II)-Catalyzed Oxidation of gem-Difluoroalkenes Generate α,α-Difluorinated-α-Phenoxyketones

Koley, S.; Cayton, K. T.; González-Montiel, G. A.; Yadav, M. R.; Orsi, D. L.; Intelli, A. J.; Cheong, P. H.-Y.;* Altman, R. A.*

J. Org. Chem. 2022, 87, 10710–10725.

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42. Fluorine-Retentive Strategies for the Functionalization of gem-Difluoroalkenes

Sorrentino, J. P.; Altman, R. A.*

Synthesis 2021, 53, 3935–3950.

41. Acid-catalyzed Hydrothiolation of gem-Difluorostyrenes to Access α,α-Difluoroalkylthioethers
41. Acid-catalyzed Hydrothiolation of gem-Difluorostyrenes to Access α,α-Difluoroalkylthioethers

Sorrentino, J. P.; Orsi, D. L.; Altman, R. A.*

J. Org. Chem. 2021, 86, 2297–2311.

39. Arylation of gem-difluoroalkenes using a Pd/Cu Co-catalytic system that avoids β-fluoride elimination
39. Arylation of gem-difluoroalkenes using a Pd/Cu Co-catalytic system that avoids β-fluoride elimination

Yuan, K.; Feoktistova, T.; Cheong, P. H.-Y.;* Altman, R. A.*

Chem. Sci. 2021, 12, 1363–1367.

38. Cobalt-Catalyzed Selective Unsymmetric Dioxidation of β,β-Difluorostyrenes
38. Cobalt-Catalyzed Selective Unsymmetric Dioxidation of β,β-Difluorostyrenes

Orsi, D. L.; Sorrentino, J. P.; Douglas, J. T.; Altman, R. A.*

J. Org. Chem. 2020, 85, 10451–10465.

36. Recent Advances in Transition Metal Catalyzed Functionalization of gem-Difluoroalkenes
36. Recent Advances in Transition Metal Catalyzed Functionalization of gem-Difluoroalkenes

Koley, S.; Altman, R. A.*

Isr. J. Chem. 2020, 60, 313–339.

35. Connecting Remote C–H Bond Functionalization and Decarboxylative Coupling Using Simple Amines
35. Connecting Remote C–H Bond Functionalization and Decarboxylative Coupling Using Simple Amines

de Azambuja, F.; Yang, M.-H.; Feoktistova, T.; Selvaraju, M.; Brueckner, A. C.; Grove, M. A.; Koley, S.; Cheong, P. H.-Y.;* Altman, R. A.*

Nature Chem. 2020, 12, 489–496.

33. BBDFA: A Practical Reagent for Trifluoromethylation of Allylic and Benzylic Alcohols on Preparative Scale
33. BBDFA: A Practical Reagent for Trifluoromethylation of Allylic and Benzylic Alcohols on Preparative Scale

Han, C.;* Alabanza, L. M.; Kelly, S. M.; Orsi, D. L.; Gosselin, F.; Altman, R. A.*

Org. Proc. Res. Dev. 2019, 23, 1695–1702.

32. Organocatalytic Strategy for Hydrophenolation of gem-Difluoroalkenes
32. Organocatalytic Strategy for Hydrophenolation of gem-Difluoroalkenes

Orsi, D. L.; Yadav, M. R.; Altman, R. A.*

Tetrahedron 2019, 75, 4325–4336.

31. Synthesis of C2-Deutero-L-Tryptophan by Sequential Ir-Catalyzed Reactions
31. Synthesis of C2-Deutero-L-Tryptophan by Sequential Ir-Catalyzed Reactions

Vallakati, R. K.; Plotnikov, A. T.; Altman, R. A.*

Tetrahedron 2019, 75, 2261–2264.

30. Catalytic One-Step Deoxytrifluoromethylation of Alcohols
30. Catalytic One-Step Deoxytrifluoromethylation of Alcohols

de Azambuja, F.; Lovrien, S. K.; Ross, P.; Ambler, B. R.; Altman, R. A.*

J. Org. Chem. 2019, 84, 2061–2071.

26. Exploiting the Unusual Effects of Fluorine in Methodology
26. Exploiting the Unusual Effects of Fluorine in Methodology

Orsi, D. L.; Altman, R. A.*

Chem. Commun. 2017, 53, 7168–7181.

25. Base Catalysis Enables Access to α,α-Difluoroalkylthio-ethers
25. Base Catalysis Enables Access to α,α-Difluoroalkylthio-ethers

Orsi, D. L.; Easley, B. J.; Lick, A. M.; Altman, R. A.*

Org. Lett. 2017, 19, 1570–1573.

23. Metal-catalyzed Decarboxylative Fluoroalkylation Reactions
23. Metal-catalyzed Decarboxylative Fluoroalkylation Reactions

Ambler, B. R.; Yang, M.-H.; Altman, R. A.*

Synlett 2016, 27, 2747–2755.

22. Palladium Catalysis Enables Benzylation of α,α-Difluoroketone Enolates
22. Palladium Catalysis Enables Benzylation of α,α-Difluoroketone Enolates

Yang, M.-H.; Hunt, J. R.; Sharifi, N.; Altman, R. A.*

Angew. Chem. Int. Ed. 2016, 55, 9080–9083.

21. Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates
21. Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates

Ambler, B. R.; Zhu, L.; Altman, R. A.*

J. Org. Chem. 2015, 80, 8449–8457.

20. Ligand-controlled Regioselective Cu-Catalyzed Trifluoromethylation to Generate Trifluoromethyl Allenes
20. Ligand-controlled Regioselective Cu-Catalyzed Trifluoromethylation to Generate Trifluoromethyl Allenes

Ambler, B. R.; Peddi, S.; Altman, R. A.*

Org. Lett. 2015, 17, 2506–2509.

19. Ligand-Controlled Regiodivergent Palladium-catalyzed Decarboxylative Allylation Reaction to Access α,α-Difluoroketones
19. Ligand-Controlled Regiodivergent Palladium-catalyzed Decarboxylative Allylation Reaction to Access α,α-Difluoroketones

Yang, M.-H.; Orsi, D.; Altman, R. A.*

Angew. Chem. Int. Ed. 2015, 54, 2361–2365.

18. Metal-free Trifluoromethylation of Aromatic and Heteroaromatic Aldehydes and Ketones
18. Metal-free Trifluoromethylation of Aromatic and Heteroaromatic Aldehydes and Ketones

Qiao, Y.; Si, T.; Yang, M.-H.; Altman, R. A.*

J. Org. Chem. 2014, 79, 7122–7131.

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