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Picazo Laboratory

Publications

23. A. Talim G. K; Kizirian, M.; Picazo, E. Strategies for Enantioselective, Cascade, Valorizing, and Expanded Heterocyclic Piancatelli Rearrangements. ACS Org. Inorg. Au 2026, accepted. DOI: 10.1021/acsorginorgau.6c00050
– [Invited, Special Issue] In honor of Prof. Elias Picazo and his 2026 ACS Organic & Inorganic Rising Stars Award
– An ACS Editors' Choice Article

22. Reyes, C. A.; Ramsperger, C. A.; Shao, A.; Hoye, P.; Karr, A.; Picazo, E. Stenhouse Zwitterion Photoswitches as Hydrogen-Bond Acceptors.
• J. Am. Chem. Soc. 2026, 148, 21973–21982. DOI: 10.1021/jacs.6c03702
• Preprint: ChemRxiv 2026, DOI: 10.26434/chemrxiv.15000976/v1

21. Karr, A.; Picazo, E. Metal-Free Hydrogen Atom Transfer for Direct Thiolation of Hydridic α- C(sp3)−H Bonds.
• Preprint: ChemRxiv 2026, DOI: 10.26434/chemrxiv.15002696/v1

C–Sphoto.png

20. Semenya, J.; Picazo, E. Amino-Acid-Derived Androgen Receptor Modulators.
• ACS Med. Chem. Lett. 2026, 17, 1421–1426. DOI: 10.1021/acsmedchemlett.6c00227

19. Biv, K.; Lin, W.; White, K. L.; Picazo, E. Amino Donor-Acceptor Stenhouse Adducts as Visible-Light-Responsive Intrinsically Emissive Photoswitches for Dynamic Cellular Imaging.
• Adv. Funct. Mater. 2026, e75800. DOI: 10.1002/adfm.75800
• Preprint: ChemRxiv 2026, DOI: 10.26434/chemrxiv.15000027/v1

18. Karr, A.; Lee, H.; K, A. T. G.; Ramsperger, C. A.; Reyes, C. A.; Biv, K.; Picazo, E. Sulfonyl-Tuned Amino DASAs for Targeted Photophysical and Photoswitching Control.
• Chem. Sci. 2026, 17, 3189–3197. DOI: 10.1039/D5SC07740K
• Preprint: ChemRxiv 2025, DOI: 10.26434/chemrxiv-2025-w75zj

17. Yang, Y.; Zhang, M.; Picazo, E. Iron-Mediated C(sp3) Transthioetherification.
• Tetrahedron 2025, 187, 134937. DOI: 10.1016/j.tet.2025.134937
– [Invited, Special Issue] In honor of Prof. Eric Jacobsen and his 2024 Tetrahedron Prize for Creativity in Organic Chemistry

16. Semenya, J.; Yang, Y.; Lee, H.; Giannantonio, K. A.; Manduva, R.; Picazo, E. C(sp3)–Heteroatom Bond Formation by Iron-Catalyzed Soft Couplings.
• Commun. Chem. 2025, 8, 73. DOI: 10.1038/s42004-025-01478-2
• Preprint: ChemRxiv 2024, DOI: 10.26434/chemrxiv-2024-r9sdv

CommunChem

15. Reyes, C. A.; Karr, A.; Ramsperger, C. A.; K, A. T. G.; Lee, H.; Picazo, E. Compartmentalizing Donor–Acceptor Stenhouse Adduct Photoswitches for Structure–Property Relationship Analysis.
• J. Am. Chem. Soc. 2025, 147, 10–26. DOI: 10.1021/jacs.4c14198
– A JACS Most Read Article

14. Semenya, J.; Yang, Y.; Picazo, E. Iron-Catalyzed Cross-Electrophile Coupling.
• [Invited SYNPACTS Article] Synlett 2025, 36, 755–758. DOI: 10.1055/s-0043-1775420
– A Synlett Most Read Article
• [Original Article] J. Am. Chem. Soc. 2024, 146, 4903–4912. DOI: 10.1021/jacs.3c13984
– A JACS Most Read Article

13. Beyer, P. D.; Nielsen, M. M.; Picazo, E.; Jacobsen E. N. β-Selective 2-Deoxy- and 2,6-Dideoxyglucosylations Catalyzed by Bis-Thioureas.
• J. Am. Chem. Soc. 2024, 146, 27318–27323. DOI: 10.1021/jacs.4c11560
• Preprint: ChemRxiv 2024, DOI: 10.26434/chemrxiv-2024-7414b

12. Grotsch, K.; Sadybekov, A. V.; Hiller, S.; Zaidi, S.; Eremin, D.; Le, A.; Liu, Y.; Smith, E. C.; Illiopoulis-Tsoutsouvas, C.; Thomas, J.; Aggarwal, S.; Pickett, J. E.; Reyes, C.; Picazo, E.; Roth, B. L.; Makriyannis, A.; Katritch, V.; Fokin, V. V. Virtual Screening of a Chemically Diverse “Superscaffold” Library Enables Ligand Discovery for a Key GPCR Target.
• ACS Chem. Biol. 2024, 19, 866–874. DOI: 10.1021/acschembio.3c00602

11. Reyes, C. A.; Lee, H.; Karanovic, C.; Picazo, E. Development and Characterization of Amino Donor-Acceptor Stenhouse Adducts.
• Nat. Commun. 2024, 15, 5533. DOI: 10.1038/s41467-024-49808-7
– Featured in Springer Nature's "Behind the Paper"
– Featured by USC Chemistry
– Featured by Thieme's Synform
• Preprint: ChemRxiv 2024, DOI: 10.26434/chemrxiv-2024-ln2kk

Amino DASAs.png

10. Semenya, J.; Yang, Y.; Picazo, E. Cross-Electrophile Coupling of Benzyl Halides and Disulfides Catalyzed by Iron.
• J. Am. Chem. Soc. 2024, 146, 4903–4912. DOI: 10.1021/jacs.3c13984
– A JACS Most Read Article
– Featured by USC Chemistry
– Featured by Thieme's Synpacts
• Preprint: ChemRxiv 2023, DOI: 10.26434/chemrxiv-2023-2jvp6

Prior to USC

9. Ohashi, M.; Jamieson, C. S.; Cai, Y.; Tan, D.; Kanayama, D.; Tang, M.-C.; Anthony, S. M.; Chari, J. V.; Barber, J. S.; Picazo, E.; Kakule, T. B.; Cao, S.; Garg, N. K.; Zhou, J.; Houk, K. N.; Tang, Y. An Enzymatic Alder-Ene Reaction. Nature 2020, 586, 64–69.

8. Strassfeld, D. A.; Wickens, Z. K.; Picazo, E.; Jacobsen, E. N. Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to Oxetanes. J. Am. Chem. Soc. 2020, 142, 9175–9180.

7. Kearney, S. E.; Zahoránszky-Kőhalmi, G.; Brimacombe, K. R.; Henderson, M. J.; Lynch, C.; Zhao, T.; Wan, K. K.; Itkin, Z.; Dillon, C.; Shen, M.; Cheff, D. M.; Lee, T. D.; Bougie, D.; Cheng, K.; Coussens, N. P.; Dorjsuren, D.; Eastman, R. T.; Huang, R.; Iannotti, M. J.; Karavadhi, S.; Klumpp-Thomas, C.; Roth, J. S.; Sakamuru, S.; Sun, W.; Titus, S. A.; Yasgar, A.; Zhang, Y.-Q.; Zhao, J.; Andrade, R. B.; Brown, M. K.; Burns, N. Z.; Cha, J. K.; Mevers, E. E.; Clardy, J.; Clement, J. A.; Crooks, P. A.; Cuny, G. D.; Ganor, J.; Moreno, J.; Morrill, L. A.; Picazo, E.; Susick, R. B.; Garg, N. K.; Goess, B. C.; Grossman, R. B.; Hughes, C. C.; Johnston, J. N.; Joullie, M. M.; Kinghorn, A. D.; Kingston, D. G. I.; Kriche, M. J.; Kwon, O.; Maimone, T. J.; Majumdar, S.; Maloney, K. N.; Mohamed, E.; Murphy, B. T.; Nagorny, P.; Olson, D. E.; Overman, L. E.; Brown, L. E.; Snyder, J. K.; Porco Jr., J. A.; Rivas, F.; Ross, S. A.; Sarpong, R.; Sharma, I.; Shaw, J. T.; Xu, Z.; Shen, B.; Shi, W.; Stephenson, C. R. J.; Verano, A. L.; Tan, D. S.; Tang, Y.; Taylor, R. E.; Thomson, R. J.; Vosburg, D. A.; Wu, J.; Wuest, W. M.; Zakarian, A.; Zhang, Y.; Ren, T.; Zuo, Z.; Inglese, J.; Michael, S.; Simeonov, A.; Zheng, W.; Shinn, P.; Jadhav, A.; Boxer, M. B.; Hall, M. D.; Xia, M.; Guha, R.; Rohde, J. M. Canvass: A Crowd-Sourced, Natural Product Screening Library for Exploring Biological Space. ACS Central Science 2018, 4, 1727–1741.

6. Picazo, E.†; Anthony, S. M.†; Giroud, M.; Simon, A.; Miller, M. A.; Houk, K. N.; Garg, N. K. Arynes and Cyclic Alkynes as Synthetic Building Blocks for Stereodefined Quaternary Centers. J. Am. Chem. Soc. 2018, 140, 7605–7610.

5. Picazo, E.; Morrill, L. A.; Susick, R. B.; Moreno, J.; Smith, J. M.; Garg, N. K. Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies. J. Am. Chem. Soc. 2018, 140, 6483–6492.

4. Simmons, B. J.; Hoffmann, M.; Champagne, P. A.; Picazo, E.; Yamakawa, K.; Morrill, L. A.; Houk, K. N.; Garg, N. K. Understanding and Interrupting the Fischer Azaindolization Reaction. J. Am. Chem. Soc. 2017, 139, 14833–14836.

3. Susick, R. B.†; Morrill, L. A.†; Picazo, E.†; Garg, N. K. Pardon the Interruption: A Modification of Fischer’s Venerable Reaction for the Synthesis of Heterocycles and Natural Products. Synlett 2017, 28, 1–11.

2. Moreno, J.†; Picazo, E.†; Morrill, L. A.; Smith, J. M.; Garg, N. K. Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (−)-2(S)-Cathafoline, and (−)-Aspidophylline A. J. Am. Chem. Soc. 2016, 138, 1162–1165.

1. Picazo, E.; Houk, K. N.; Garg, N. K. Computational Predictions of Substituted Benzyne and Indolyne Regioselectivities. Tetrahedron Lett. 2015, 56, 3511–3514.

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