Publications from the Wang Group

53. Nguyen, A.; Zhang, J.; Huang, S.; Wang, Q.* Copper-Catalyzed 1,3-Aminocyclization of Cyclopropanes as A Rapid Entry to gamma-Amino Heterocycles. Org. Lett. 2024, 26, 9508–9512.

52. Watkins, N.H.; Kwon, Y.; Wang, Q.* Copper-Catalyzed 1,4-Aminohydroxylation and Aminothiolation of 1,3-Dienes by Carbonyl-Assisted Migration. Chem Catalysis 2024, 4, 101147 (Featured article).

51. Feng, G.; Wang, Q.* Enantioselective synthesis of axially chiral P-containing allenes for allenyl chirality. Chem Catalysis 2024, 4 (3), 100954 (invited Preview).

50. Cho, S.; Bitting, K. J. Wang, Q.* Deprotonative C–H Zincation for Carbon–Carbon Bond Formation.  Handbook of C–H-Functionalization, Wiley-VCH: 2023. DOI: 10.1002/9783527834242.chf0197

49. Feng, G.; Ku, C. K.; Zhao, J.; Wang, Q.* Copper-Catalyzed Regioselective Aminofluorination of Alkenes and 1,3-Dienes: Direct Entry to Diverse β-Fluoroamines.  J. Am. Chem. Soc., 2022, 144, 20463−20471.

48. Park, H.; # Jun Chen,# J.; Dimitrov, I. E.; Park J. M.;* Wang, Q.* Design and Characterization of Hyperpolarized 15N-BBCP as a H2O2-Sensing Probe. ACS Sensors, 2022, 7, 2928−2933.

47. Park, H.; # Eriksson. S., # Warren, S. W.;*  Wang, Q.* "Design, Synthesis and Evaluation of 15N- and 13C-Labeled Molecular Probes as Hyperpolarized Nitric Oxide Sensors." Bioorg. Med. Chem. 2022, 72, 116969. (# equal contribution).

  • Special issue in honor of Yimon Aye’s 2022 Tetrahedron Young Investigator Award.

46. Kwon, Y.; Wang, Q.* "Recent Advances in 1,2-Amino(hetero)arylation of Alkenes" Chemistry - An Asian Journal, 2022, 17, e202200215.

  • Special Collection on Women in Chemistry.

45. Park, H.; Wang, Q.* "State-of-the-Art Accounts of Hyperpolarized 15N-Labeled Molecular Imaging Probes for Magnetic Resonance Spectroscopy and Imaging" Chem. Sci. 2022, 13, 7378–7391.

44. Cho, S.; McLaren, E.J.; Wang, Q.* "Three-Component Difunctionalization of Cyclohexenyl Triflates Direct Access to Versatile Cyclohexenes via Cyclohexynes" Angew. Chem. Int. Ed. 2021, 60, 26332–26336

  • Selected as a Hot Paper.

43. Bae,J.; # Zhang, G.; # Park, H.; Warren, S. W.;* Wang, Q.* "15N-Azides as Practical and Effective Tags for Developing Long- Lived Hyperpolarized Agents" Chem. Sci. 2021, 12, 14309–14315 (# equal contribution).

42. Kwon, Y.;# Zhang, W.;# Wang, Q.* "Copper-Catalyzed Aminoheteroarylation of Unactivated Alkenes through Distal Heteroaryl Migration" ACS Catal. 2021, 11, 8807–8817.

  • Top 10 Most Read Articles, July 2021

41. Wang, L.; Wang, H.; Shen, K.; Park, H.; Zhang, T.; Wu, X.; Hu, M.; Yuan, H.; Yue Chen, Y.; Wu, Z.*, Wang, Q.*, Li, Z. Development of novel 18F-PET agents for tumor hypoxia imaging J. Med. Chem. 2021, 64, 5593−5602.

40. Zhang, W.;# Wang, C.;# Wang, Q.* Copper-Catalyzed Decarboxylative Functionalization of Conjugated β,γ-Unsaturated Carboxylic Acids ACS Catal. 2020, 10, 13179–13185. (# equal contribution).

39. Kwon, Y.; Wang, Q.* “Copper-Catalyzed 1,2-Aminocyanation of Unactivated Alkenes via Cyano Migration” Org. Lett. 2020 11, 4141–4145.

38. Park, H.;# Zhang, G.; # Bae,J.; # Theis, T.; Warren, S. W.;* Wang, Q.* Application of 15N2-Diazirines as a Versatile Platform for Hyperpolarization of Biological Molecules by d-DNP. Bioconjugate Chem. 2020, 31, 537–541 (# equal contribution)

37. Cho, S.; Wang, Q.* 1,2-Difunctionalization of Aryl Triflates: A Direct and Modular Access to Diversely Functionalized Anilines. Org. Lett. 2020, 22, 1670–1674.

36. Hemric, B.N.; Ku, C. K.; and Wang, Q.* O-Benzoyl-N-Hydroxylmorpholine. In Encyclopedia of Reagents for Organic Synthesis. Wiley-VCH: 2020. DOI:10.1002/047084289X.rn02290

35. Park, H.;# Urs, A. N.;# Zimmerman, J.; Liu, C.; Wang, Q.* Urs, N.M.* Structure-Functional-Selectivity Relationship Studies of Novel Apomorphine Analogs to Develop D1/D2R Biased Ligands. ACS Med. Chem. Lett. 2020,11, 385–392 (# equal contribution).

34. Hemric, B. N.; Chen, A.; Wang, Q.* Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction with O-Acylhydroxylamines and Carboxylic Acids. ACS Catal. 2019, 10070–10076.

33. Hemric, B. N.; Chen, A.; Wang, Q.* Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons. J. Org. Chem., 2019, 84, 1468–1488.

32. Cho, S.; Wang, Q.* ortho-Difunctionalization of arynes by LiZnEt2(TMP)-mediated deprotonative zincation/elimination of aryl triflates. Tetrahedron, 2018, 74 (26), 3325–3328.

  • Special issue in honor of Seth Herzon’s Tetrahedron Young Investigator Award.

31. Liu, C; Wang, Q.* Alkenylation of sp3 C-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts. Angew. Chem. Int. Ed. 2018, 57, 4727 –4731.

30. Bae, J.;# Zhou, Z.,# Theis, T.,* Warren, W. S., Wang, Q.*15N4-1,2,4,5-tetrazines as potential molecular tags: Integrating bioorthogonal chemistry with hyperpolarization and unearthing para-N2 Sci. Adv. 2018, 4, eaar2978 (# equal contribution).

29. Ortiz, G. X.;# Chansaenpak, K.;# Wang, M.; Ma, X.; Wang, H.; Li, Z.;* Wang, Q.* A Novel 18F-Labeling Method for the Synthesis of [18F]-Piperidine-Containing Ligands as Potential PET Radiotracers for Sigma Receptors. Synlett, 2018, 28, 410–414.(# equal contribution)

  • Contribution to the Cluster Alkene Halofunctionalization.

28. Shen, K.; Wang, Q.* Copper-Catalyzed Aminoalkynylation of Alkenes with Hypervalent Iodine Reagents Chem. Sci., 2017, 8, 8265–8270.

27. Shen, K.; Wang, Q.* Copper-Catalyzed Alkene Aminoazidation as a Rapid Entry to 1,2-Diamines and Installation of an Azide Reporter onto Azahetereocycles" J. Am. Chem. Soc., 2017, 139, 13110–13116. DOI: 10.1021/jacs.7b06852

  • Top 20 Most Read Articles in Sept and Oct 2017.

26. Hendrick, C. E.; Bitting, K. J.; Cho, S.; Wang, Q.* Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation" J. Am. Chem. Soc., 2017, 139, 11622–11628. DOI: 10.1021/jacs.7b07661

25. Shen, K.;# Logan, A. W. J.;# Colell, J. F. P.;# Bae, J.; Ortiz, G. X., Jr.; Theis, T.; Warren, W. S.;* Malcolmson, S. J.;* Wang, Q.* Diazirines as Potential Molecular Imaging Tags: Probing the Requirements for Efficient and Long-Lived SABRE-Induced Hyperpolarization. Angew. Chem. Int. Ed. 2017, 56, 12112–12116. (# equal contribution)

  • Selected as Very Important Paper and highlighted on Front Cover.

24. Colell, J. F. P.; Emondts, M.; Logan, A. W. J.; Shen, K.; Bae, J.; Shchepin, R. V.; Ortiz, G. X., Jr.; Spannring, P.; Wang, Q.; Malcolmson, S. J.; Chekmenev, E. Y.; Feiters, M. C.; Rutjes, F.; Blumich, B.; Theis, T.;* Warren, W. S.* "Direct Hyperpolarization of Nitrogen-15 in Aqueous Media with Parahydrogen in Reversible Exchange" J. Am. Chem. Soc. 2017, 139, 7761–7767. DOI: 10.1021/jacs.7b0056

23. Ortiz, Jr. G. X.; Hemric, B. N.; Wang, Q.* Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides. Org. Lett. 2017, 19, 1314–1317. DOI: 10.1021/acs.orglett.7b00358

22. Colell, J. F. P. J.; Logan, A. W. J.; Zhou, Z.; Shchepin, R. V.; Barskiy, D.A.; Ortiz, G. X. Jr.; Wang, Q.; Malcolmson, S. J.; Chekmenev, E. Y.; Warren, W. S.;* Theis, T. * Generalizing, Extending, and Maximizing Nitrogen-15 Hyperpolarization induced by Parahydrogen in Reversible Exchange. J. Phy. Chem. C, 2017, 121, 6626–6634. DOI: 10.1021/acs.jpcc.6b12097

  • Front cover article in the issue of March 30, 2017.

21. Hendrick, C. E.; Wang, Q.* Emerging Developments Using Nitrogen-Heteroatom Bonds as Amination Reagents in the Synthesis of Aminoarenes. J. Org. Chem. Synopsis. 2017, 82, 839−847. DOI: 10.1021/acs.joc.6b02792

  • Top 20 Most Read Articles in Feb 2017.

20. Liu, C; Wang, Q.* Arylation, Vinylation, and Alkynylation of Electron-Deficient (Hetero)arenes Using Iodonium Salts. Org. Lett. 2016, 18, 5118–5121. DOI: 10.1021/acs.orglett.6b02550

19. Hemric, B. N.; Shen, K.; Wang, Q.* Copper-Catalyzed Amino Lactonization and Amino Oxygenation of Alkenes Using O-Benzoylhydroxylamines. J. Am. Chem. Soc. 2016, 138, 5813–5816. DOI: 10.1021/jacs.6b02840

  • Top 20 Most Read Articles May–June 2016; Highlighted in Synfacts.

18. Theis, T.;#* Ortiz Jr., G. X.;#  Logan, A.; Claytor, K.; Feng, Y.; Kuhn, W.; Blum, V.; Malcolmson, S.; Chekmenev, E. Y.; Wang, Q.;* Warren, W. S.* Direct and Cost-efficient Hyperpolarization of Long-lived Nuclear Spin States on Universal 15N2-diazirine Molecular Tags. Sci. Adv. 2016, 2, e1501438. DOI: 10.1126/sciadv.1501438. (# T.T. and G.X.O. equal contribution).

17. Hemric, B. N.; Wang, Q.* Copper-Catalyzed Intermolecular Oxyamination of Olefins Using Carboxylic Acids and O-Benzoyl hydroxylamines. Beil. J. Org. Chem. 2016, 12, 22–28. DOI:10.3762/bjoc.12.4

16. Shen, K.; Wang, Q.* Copper-Catalyzed Aminotrifluoromethylation of Alkenes: A Facile Synthesis of CF3-Containing Lactams. Org. Chem. Front. 2016, 3, 222-226. DOI: 10.1039/C5QO00353A

15. Chen, Z. L.; Wang, Q.* Synthesis of o-Aminophenols via a Formal Insertion Reaction of Arynes into Hydroxyindolinones. Org. Lett. 2015, 17, 6130–6133. DOI: 10.1021/acs.orglett.5b03147

14. McDonald, S. L.; Hendrick, C. E.; Bitting, K. J. Wang, Q.* Copper-Catalyzed Electrophilic Amination of Heteroaromatic and Aromatic C−H Bonds via tmpZnCl-LiCl Mediated Metalation. Org. Synth. 2015, 92, 356–372. DOI: 10.15227/orgsyn.092.0356

13. Shen, K.; Wang, Q.* Copper-Catalyzed Diamination of Unactivated Alkenes with Hydroxylamines. Chem. Sci., 2015, 6, 4279–4283. DOI: 10.1039/C5SC00897B

12. Hendrick, C. E.; Wang, Q.* Synthesis of ortho-Haloaminoarenes by Aryne Insertion of Nitrogen−Halide Bonds. J. Org. Chem. 2015, 80, 1059–1069. DOI: 10.1021/jo502541t

11. McDonald, S. L.; Wang, Q.* α-Amination of Phosphonates: A Direct Synthesis of α-Amino Phosphonic Acids and Derivatives. Synlett  2014, 25, 2233–2238. DOI: 10.1055/s-0034-1378324

  • Invited highlight.

10. Feng, Y.; Sokol, E.; Del Vecchio, C.; Sanduja, S.; Claessen, J.; Proia, T.; Jin, D.; Reinhardt, F.; Ploegh, H. L.; Wang, Q.; Gupta, P.* Epithelial-to-Mesenchymal Transition Activates PERK-eIF2a and Sensitizes Cells to Endoplasmic Reticulum Stress. Cancer Discov. 2014, 4, 702–715. DOI: 10.1158/2159-8290.CD-13-0945

9. Wang, B; Rao, Y.-H.; Inoue, M.; Hao, R.; Lai, C.-H.; McDonald, S. L.; Choi, M.-C.; Wang, Q.; Mari Shinohara, M.; Yao, T.-P.* Microtubule Acetylation Amplifies p38 KinaseSignalling and Anti-inflammatory IL-10 Production. Nat. Commun. 2014, 5, 3479. DOI: 10.1038/ncomms4479

8. McDonald, S. L.; Hendrick, C. E.; Wang, Q.* Copper-Catalyzed Electrophilic Amination of Heteroarenes and Arenes via C–H Zincation. Angew. Chem. Int. Ed. 2014, 53, 4667–4670. DOI: 10.1002/anie.201311029

7. McDonald, S. L.; Wang, Q.* Selective α-Amination and α-Acylation of Esters and Amides via Dual Reactivity of O-Acylhydroxylamines toward Zinc Enolates. Chem. Comm. 2014, 50, 2535–2538. DOI: 10.1039/c3cc49296f

6. Ortiz Jr., G. X.; Kang, B.; Wang, Q.* One-Pot Synthesis of 3-Azido- and 3-Aminopiperidines by Intramolecular Cyclization of Unsaturated Amines. J. Org. Chem. 2014, 79, 571–581. DOI: 10.1021/jo4022666

  • Top 10 Most Read Articles in Jan 2014.

5. McDonald, S. L.; Wang, Q.* Copper-Catalyzed alpha-Amination of Phosphonates and Phosphine Oxides: A Direct Approach to alpha-Amino Pho sphonic Acids and Derivatives. Angew. Chem. Int. Ed. 2014, 53, 1867–1871. DOI: 10.1002/anie.201308890

4. Hendrick, C. E.; McDonald, S. L.; Wang, Q.* Insertion of Arynes into N-Halo Bonds: A Direct Approach to ortho-Halo aminoarenes. Org. Lett. 2013, 15, 3444–3447. DOI: 10.1021/ol401518c

3. Hill, N.; Du, L.; Wang, Q.* DOS-Derived Small-Molecule Probes in Chemical Biology In Diversity-Oriented Synthesis: Basics and Applications in Organic Synthesis, Drug Discovery, and Chemical Biology, Trabocchi, A., Ed. Wiley-VCH: 2013. DOI: 10.1002/9781118618110.ch18

2. Feng, Y; Theis, T.; Liang, X.; Davis, R. M.; Wang, Q.; Zhou, P.; Warren, W. S.*  Storage of Hydrogen Spin Polarization in Long-Lived 13C2 Singlet Order and Implications for Hyperpolarized Magnetic Resonance Imaging. J. Am. Chem. Soc. 2013, 135, 9632−9635. DOI: 10.1021/ja404936p

1. Huang, H.-T.; Lacy, T. L.; Blachut, B.; Ortiz Jr., G. X.; Wang, Q.* An Efficient Synthesis of Fluorinated Azaheterocycles by Aminocyclization of Alkenes. Org. Lett. 2013, 15, 1818–1821. DOI: 10.1021/ol4003866

  • Top 10 Most Read Articles in April and Q2 2013.

 

Publications before independent career

  1. Dass, F. M.; Kemp, M.; Schroeder, F. A; Wagner, F. F.; Wang, Q.; Holson, E. B.* Histone Acetylation and Deacetylation. In Epigenetic Regulation and Epigenomics, Meyers, R. A., Ed. Wiley-VCH: Weinheim, Germany, 2012. DOI: 10.1002/3527600906.mcb.201100036
  2. Yuan, Y.; Tang, A. J.; Castoreno, A. B.; Kuo, S.-Y.; Wang, Q.; Kuballa, P.; Xavier, R.; Shamji, A; Schreiber, S. L.; Wagner, B. K. Gossypol and an HMT G9a Inhibitor Act in Synergy to Induce Cell Death in Pancreatic Cancer Cells. Cell Death Dis. 2013, 4, e690.
  3. Yuan, Y.;* Wang, Q.;* Paulk, J.; Kubicek, S.; Kemp, M.; Adams, D.; Shamji, A; Wagner, B. K.; Schreiber, S. L. A Small-Molecule Probe of the Histone Methyltransferase G9a Induces Cellular Senescence in Pancreatic Adenocarcinoma. ACS Chem. Biol. 2012, 7, 1152-1157.
  4. Kemp, M; Wang, Q.; Fuller, F. H.; West, N.; Martineza, N. M.; Morsea, El. M.; Weïwera, M.; Schreiber, S. L.; Bradner, J. E.; Koehler, A. K. A Novel HDAC Inhibitor with a Hydroxy-Pyrimidine Scaffold. Bioorg. Med. Chem. Lett. 2011, 21, 4164-4169.
  5. Wang, Q.; Schreiber, S. L. Copper-Mediated Amidation of Heterocyclic and Aromatic C-H Bonds. Org. Lett., 2009, 11, 5178-5180.
  6. Sun, C.; Wang, Q.; Brubaker, J. D.; Wright, P. M.; Lerner, C. D.; Noson, K.; Charest, M.; Siegel, D. R.; Wang, Y.-M.; Myers, A. G. A Robust Platform for the Synthesis of New Tetracycline Antibiotics. J. Am. Chem. Soc., 2008, 130, 17913-17927.
  7. Padwa, A.; Wang, Q. Synthesis of the Tetracyclic Framework of the Erythrina Alkaloids Using a [4 + 2]-Cycloaddition/Rh(I)-Catalyzed Cascade of 2-Imidofurans. J. Org. Chem. 2006, 71, 7391-7402.
  8. Padwa, A.; Wang, Q. Rhodium(I)-Catalyzed Nucleophilic Ring-Opening Reactions of Oxabicyclo Adducts Derived from the [4 + 2]-Cycloaddition of 2-Imido-Substituted Furans. J. Org. Chem. 2006, 71, 3210-3220.
  9. Wang, Q.; Padwa, A. Synthesis of the Erythrina Alkaloid 3-Demethoxyerythratidinone. Novel Acid-Induced Rearrangements of Its Precursors. Org. Lett. 2006, 8, 601-604.
  10. Padwa, A.; Nara, S.; Wang, Q. Additive Pummerer Reaction of Heteroaromatic Sulfilimines with Carbon Nucleophiles. Tetrahedron Lett. 2006, 47, 595-597.
  11. Padwa, A.; Nara, S.; Wang, Q. Dichloroketene-Induced Cyclizations of Vinyl Sulfilimines: Application of the Method in the Synthesis of (±)-Desoxyeseroline. J. Org. Chem. 2005, 70, 8538-8549.
  12. Wang, Q.; Nara, S.; Padwa, A. A New Synthesis of ɣ-Lactams Based on the Reaction of Vinyl Sulfilimines with Dichloroketene. Org. Lett. 2005, 7, 839-841.
  13. Wang, Q.; Padwa, A. Rh(I)-Catalyzed Ring Opening of an IMDAF-Derived Oxabicyclo cycloadduct as the Key Step in the Synthesis of (±)-epi-Zephyranthine. Org. Lett. 2004, 6, 2189-2192.
  14. Padwa, A.; Brodney, M. A.; Lynch, S. M.; Rashatasakhon, R.; Wang, Q.; Zhang, H. A New Strategy toward Indole Alkaloids Involving an Intramolecular Cycloaddition/Rearrangement Cascade. J. Org. Chem. 2004, 69, 3735-3745.
  15. Padwa, A.; Heidelbaugh, T. M.; Kuethe, J. T.; McClure, M. S.; Wang, Q. Tandem Pummerer/Mannich Cyclization Cascade of a-Sulfinylamides as a Method to Prepare Aza-Heterocycles. J. Org. Chem. 2002, 67, 5928-5937.

Patent

  • Myers, A. G.; Brubaker, J. D.; Sun, C.; Wang, Q. Synthesis of Tetracyclines and Analogues Thereof. (WO/2007/117639).

CONTACT INFORMATION

Qiu Wang
Professor of Chemistry, Duke University
124 Science Drive, Durham, NC 27708-0347
Phone: 919-660-1648 Email: qiu.wang at duke.edu
Copyright © The Wang Group. All Rights Reserved.

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