Publications

2020 — Present

Featured
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

Andrew J. Intelli, Jacob P. Sorrentino, and Ryan A. Altman*

Org. Synth. 2024, 101, 542. DOI: 10.15227/orgsyn.101.0542.

53. A Phenotypic High-Throughput Screen Identifies Small Molecule Modulators of Endogenous RGS10 in BV-2 Cells
53. A Phenotypic High-Throughput Screen Identifies Small Molecule Modulators of Endogenous RGS10 in BV-2 Cells

Talele, S.; Gonzalez, S.; Trudeau, J.; Junaid, A.; Loy, C.; Altman, R. A.; Sjogren, J. B.*

J. Med. Chem., 2024, 67, 20343–20352.

52. α-Amino-β-Carboxymuconate-ε-Semialdehyde Decarboxylase Catalyzes Enol/Keto Tautomerization of Oxaloacetate
52. α-Amino-β-Carboxymuconate-ε-Semialdehyde Decarboxylase Catalyzes Enol/Keto Tautomerization of Oxaloacetate

Yang Y., Davis I., Altman R. A., Liu A.

J. Biol. Chem., 2024, 300, 107878.

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, 19, 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, 21, 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.

44. Fluoroalkylation of Dextromethorphan Improves CNS Exposure and Metabolic Stability
44. Fluoroalkylation of Dextromethorphan Improves CNS Exposure and Metabolic Stability

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

ACS Med. Chem. Lett. 2022, 13, 707–713.

43. Modulating β-Arrestin-2 Recruitment at the δ- and μ-Opioid Receptors
43. Modulating β-Arrestin-2 Recruitment at the δ- and μ-Opioid Receptors

Sharma K. S.; Cassell, R. J.; Meqbil, Y. J.; Su, H.; Blaine, A. T.; Cummins, B. R.; Mores, K. L.; Johnson, D.; van Rijn, R. M.;* Altman, R. A.*

RSC Med. Chem. 2021, 12, 1958–1967.

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

40. Diflunisal Derivatives as Modulators of ACMS Decarboxylase Targeting the Tryptophan-Kynurenine Pathway
40. Diflunisal Derivatives as Modulators of ACMS Decarboxylase Targeting the Tryptophan-Kynurenine Pathway

Yang, Y.; Borel, T.; de Azambuja, F.; Johnson, D.; Sorrentino, J. P.; Udokwu, C.; Davis, I.; Liu, A.;* Altman, R. A.*

J. Med. Chem. 2021, 64, 797–811.

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.

37. Late-Stage Conversion of a Metabolically Labile Aryl Methyl Ether-Containing Natural Product to Fluoroalkyl Analogues
37. Late-Stage Conversion of a Metabolically Labile Aryl Methyl Ether-Containing Natural Product to Fluoroalkyl Analogues

Sorrentino, J. S.; Ambler, B. R.; Altman, R. A.*

J. Org. Chem. 2020, 85, 5416–5427.

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.

Before 2020

Featured
34. The Meta-Position of Phe4 in Leu-enkephalin Regulates Potency, Selectivity, Functional Activity, and Signaling Bias at the Delta and Mu Opioid Receptors
34. The Meta-Position of Phe4 in Leu-enkephalin Regulates Potency, Selectivity, Functional Activity, and Signaling Bias at the Delta and Mu Opioid Receptors

Cassell, R. J.; Sharma K. S.; Su, H.; Cummins, B. R.; Cui, H.; Mores, K. L.; Blaine, A. T.; Altman, R. A.;* van Rijn, R. M.*

Molecules 2019, 24, 4542.

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.

29. Synthesis of Leu-Enkephalin Peptidomimetics Containing Trifluromethylalkenes as Amide Isopolar Mimics
29. Synthesis of Leu-Enkephalin Peptidomimetics Containing Trifluromethylalkenes as Amide Isopolar Mimics

Eeda, V.; Selvaraju, M.; Altman, R. A.*

J. Fluorine Chem. 2019, 218, 90–98.

28. Tyr1-ψ[(Z)CF═CH]-Gly2 Fluorinated Peptidomimetic Improves Distribution and Metabolism Properties of Leu-Enkephalin
28. Tyr1-ψ[(Z)CF═CH]-Gly2 Fluorinated Peptidomimetic Improves Distribution and Metabolism Properties of Leu-Enkephalin

Altman, R. A.;* Sharma, K. K.; Rajewski, L. G.; Toren, P. C.; Baltezor, M. J.; Pal, M.; Karad, S. N.

ACS Chem. Neurosci. 2018, 9, 1735–1742.

27. Stepwise O-Atom Transfer in Heme-based Tryptophan Dioxygenase: The Role of Substrate Ammonium in the Epoxide Ring Opening
27. Stepwise O-Atom Transfer in Heme-based Tryptophan Dioxygenase: The Role of Substrate Ammonium in the Epoxide Ring Opening

Shin, I.; Ambler, B. R.; Wherritt, D.; Griffith, W.; Maldonado, A.; Altman, R. A.; Liu, A.*

J. Am. Chem. Soc. 2018, 140, 4372–4379.

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.

24. Synthesis and Opioid Activity of Tyr1–ψ[(Z)CF=CH]–Gly2 and Tyr1–ψ[(S)/(R)-CF3CH–NH]–Gly2 Leu-enkephalin Fluorinated Peptidomimetics
24. Synthesis and Opioid Activity of Tyr1–ψ[(Z)CF=CH]–Gly2 and Tyr1–ψ[(S)/(R)-CF3CH–NH]–Gly2 Leu-enkephalin Fluorinated Peptidomimetics

Karad, S. N.; Pal, M.; Crowley, R. S.; Prisinzano, T. E.; Altman, R. A.*

ChemMedChem 2017, 12, 571–576.

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.

17. Copper-catalyzed Conversion of Propargylic Bromodifluoroacetates to Trifluoromethanes
17. Copper-catalyzed Conversion of Propargylic Bromodifluoroacetates to Trifluoromethanes

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

Synthesis 2014, 46, 1938–1946.

16. Decarboxylative Fluorination Strategies for Accessing Medicinally-Relevant Products
16. Decarboxylative Fluorination Strategies for Accessing Medicinally-Relevant Products

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

Curr. Top. Med. Chem. 2014, 14, 966–978.

15. Copper-Catalyzed Trifluoromethylation of Allylic Bromodifluoroacetic Esters
15. Copper-Catalyzed Trifluoromethylation of Allylic Bromodifluoroacetic Esters

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

Org. Lett. 2013, 15, 5578–5581.

14. Copper-Mediated Deoxygenative Trifluoromethylation of Benzylic Xanthates: Formation of C(sp3)–CF3 from an O-Based Electrophile
14. Copper-Mediated Deoxygenative Trifluoromethylation of Benzylic Xanthates: Formation of C(sp3)–CF3 from an O-Based Electrophile

Zhu, L.; Liu, S.; Douglas, J. T.; Altman, R. A.*

Chem. Eur. J. 2013, 19, 12800–12805.

13. Preparation of Fluoroalkenes via the Shapiro Reaction: Direct Access to Fluorinated Peptidomimetics
13. Preparation of Fluoroalkenes via the Shapiro Reaction: Direct Access to Fluorinated Peptidomimetics

Yang, M. H.; Matikonda, S. S.; Altman, R. A.*

Org. Lett. 2013, 15, 3894–3897.