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Publications

Independent publications

18. Ronny Gantous and Yuri Bolshan
Direct Brønsted Acid-Catalyzed Synthesis of N-Aryl-C,N-Glycosides from exo-Glycals and Anilines.
submitted

17. Arsala Butt and Yuri Bolshan
Brønsted Acid-Catalyzed Alkylation of Tetrazoles with Alcohols.
Tetrahedron Lett. 2026, 182, 156146.

16. Ronny Gantous and Yuri Bolshan
Brønsted Acid-Catalyzed Direct N-Alkylation of Anilines with Alcohols.
ChemistrySelect 2026, 11, e73649.

15. Massimo Giammarco and Yuri Bolshan
Synthesis of C,N-glycosides from exo-glycals via selective N2-1,2,3-triazole and N1-pyrazole alkylation.
Org. Biomol. Chem. 2026, 24, 6380-6384.

14. Barmaki, S.; Butt, A.; Ali, A.; Desaulniers, J.-P.; Ahmad, S.; Forrester, S.; Varley, S.; Bolshan, Y.
O-Silyl Codeine Analogues as Ligands for Opioid Receptors.
ChemistrySelect 2025, 10, e03721.

13. Jeffery Regier and Yuri Bolshan 
Synthesis of C,N-Glycosides via Brønsted Acid-Catalyzed Azidation of exo-Glycals.
J. Org. Chem. 2024, 89, 141-151.

12. Jeffery Regier, Supriya Ghanty and Yuri Bolshan
Stereoselective Palladium-Catalyzed Arylation of Exo-Glycals with Aryl Iodides
J. Org. Chem. 2022, 87, 524–530.

 joc-2021-abstract.tif

11. Mona Almaghrabi and Yuri Bolshan
Metal-Free Derivatization of Benzhydrols with Organosilanes
ChemistrySelect 2022, 7, e202103928

mona-2021.png

10. Samira Barmaki, Arlene Ali, Jean-Paul Desaulniers and Yuri Bolshan
Bromination of codeine and its derivatives: Revisitng a 95 year old process
Tetrahedron Lett. 2020, 61, 152234.

 samira-tl-2021.png

9. Dylan H. Harris, Renata Barichello and Yuri Bolshan
Brønsted Acid-Catalyzed Alkenylation of Salicylaldehydes with Vinylboronic Acids: Synthesis of 1,4-Dienes and 2H-Chromenes
Eur. J. Org. Chem. 2020, 6000−6003.

harris-ejoc-2020.png

8. Jeffery Regier, Robert Maillet and Yuri Bolshan
A Direct Brønsted Acid-Catalyzed Azidation of Benzhydrols and Carbohydrates
Eur. J. Org. Chem. 2019, 2390−2396.

abstract

7. Ifedi Orizu and Yuri Bolshan
A General Brønsted Acid-Catalyzed Allylation of Benzhydryl Alcohols.
Tetrahedron Lett. 2016, 57, 5798-5800.

orizu allylation of alcohols

6. Kayla M. Fisher and Yuri Bolshan
Brønsted Acid-Catalyzed Direct Substitution of 2-Ethoxytetrahydrofuran with Trifluoroborate Salts.
Catalysts 2016, 6, 94-102. (invited contribution)

Fisher_catalysts

5. Kayla M. Fisher and Yuri Bolshan
Brønsted Acid-Catalyzed Reactions of Trifluoroborate Salts with Benzhydryl Alcohols.
J. Org. Chem. 2015, 80, 12676–12685.

Fisher JOC 2015

4. Matthew Baxter and Yuri Bolshan
A General Access to Propargylic Ethers through Brønsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates.
Chem. Eur. J. 2015, 21, 13535-13538.

Baxter_ChemEurJ_2015

3. Cassandra Taylor and Yuri Bolshan
Metal-free methodology for the preparation of sterically hindered alkynoylphenols and its application to the synthesis of flavones and aurones.
Tetrahedron Lett. 2015, 56, 4392-4396.

C. Taylor_2015

2. Cassandra Taylor and Yuri Bolshan
Metal-Free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts.
J. Vis. Exp. 2015, 96, e52401.
Journal of Visualized Experiments (JoVE) is the first peer reviewed scientific video journal.
http://www.jove.com/video/52401/metal-free-synthesis-ynones-from-acyl-chlorides-potassium

1. Cassandra Taylor and Yuri Bolshan
Metal-Free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts.
Org. Lett. 2014, 16, 488-491.

taylor 2013

Postdoc, PhD and Undergrad

10. Bolshan, Y.; Getlik, M.; Kuznesova, E. Wasney, G.; Hajian, T.; Poda, G.; Nguyen, K.; Wu, H.; Dombrovski, L.; Dong, A.; Schapira, M.; Arrowsmith, C.; Brown, P.; Al-awar, R.; Vedadi, M.; Smil, D.
Synthesis, Optimization, and Evaluation of Novel Small Molecules as Antagonists of WDR5-MLL Interaction.
ACS Med. Chem. Lett. 2013, 4 (3), 353-357

9. Bullwinkle, T. J.; Zou, S. B.; Rajkovic, A.; Hersch, S. J.; Elgamal, S.; Robinson, N.; Smil, D.; Bolshan, Y.; Navarre, W. W.; Ibba, M.
(R)-beta-Lysine-modified Elongation Factor P Functions in Translation Elongation.
J. Biol. Chem. 2013, 288 (6), 4416–4423.

8. Yu, W.; Smil, D.; Li, F.; Tempel, W.; Fedorov, O.; Nguyen, K. T.; Bolshan, Y.; Al-Awar, R.; Knapp, S.; Arrowsmith, C. H.; Vedadi, M.; Brown, P. J.; Schapira, M.
Bromo-deaza-SAH: a potent and selective DOT1L inhibitor.
Bioorg. Med. Chem. 2012, 21, 1787-1794.

7. Senisterra, G.; Wu, H.; Allali-Hassani, A.; Wasney, G. A.; Barsyte-Lovejoy, D.; Dombrovski, L.; Dong, A.; Nguyen, K. T.; Smil, D.; Bolshan, Y.; Hajian, T.; He, H.; Seitova, A.; Chau, I.; Li, F.; Poda, G.; Couture, J.-F.; Brown, P. J.; Al-awar, R.; Schapira, M.; R.; Arrowsmith, Vedadi, M.
Small-molecule inhibition of MLL activity by disruption of its interaction with WDR5.
Biochem. J. 2013, 449, 151–159.

6. Siarheyeva, A.; Senisterra, G.; Allali-Hassani, A.; Dong, A.; Dobrovetsky, E.; Wasney, G. A.; Chau, I.; Nguyen, K. T.; Marcellus, R.; Hajian, T.; Liu, F.; Smil, D.; Bolshan, Y.; Min, J.; Poda, G.; Bedford, M.; Brown, P. J.;  Jin, J.; Al-awar, R.; Arrowsmith, C. H.; Schapira, M.; Vedadi, M.
Discovery of an allosteric inhibitor of arginine methyltransferase PRMT3.
Structure 2012, 20, 1425-1435.

5. Bolshan, Y. and Batey, R. A.
Copper-Catalyzed Cross-Coupling of Amides and Potassium Alkenyltrifluoroborate Salts: A General Approach to the Synthesis of Enamides.
Tetrahedron 2010, 68, 5283-5294.

4. Bolshan, Y. and Batey, R. A.
Copper-catalyzed coupling of amides with potassium alkenyltrifluoroborate salts.
Angew. Chem. Int. Ed. 2008, 47, 2109-2112. (“VIP” publication)

3. Bolshan, Y.; Tomaszevski, M. and Santhakumar, V.
Thiol on silica as a 'catch and release' support for isocyanates to afford ureas.
Tetrahedron Lett. 2007, 48, 4925-4927.

2. Bolshan, Y. and Batey, R. A.
A Room-Temperature Protocol for the Rhodium(I)-Catalyzed Addition of Arylboron Compounds to Sulfinimines.
Org. Lett. 2005, 7, 1481-1484.

1. Bolshan, Y.; Chen, C.; Chilenski, J. R.; Gosselin, F.; Mathre, J.; O'Shea, P. D.; Roy, A.; Tillyer, R. D.
Nucleophilic Displacement at Benzyhydril Centers: Asymmetric Synthesis of 1,1’-Diarylalkyls Derivatives.
Org. Lett. 2004, 6, 111-114. 

Crystal Structures

Dong, A.; Dombrovski, L.; Senisterra, G.; Wernimont, A.; Wasney, G. A.; Allali Hassani, A.; Nguyen, K. T.;  Smil, D.; Bolshan, Y.; Hajian, T.; Poda, G.; Chau, I.; Al-awar, R.; Bountra, C.; Weigelt, J.; Edwards, A. M.; Arrowsmith, C. H.; Brown, P.; Schapira, M.; Vedadi, M.; Wu, H.
Crystal structure of human WD repeat domain 5 with compound.
RCSB PDB
2011, PDB ID: 3UR4.

Dong, A.; Dombrovski, L.; Wasney, G.A.; Tempel, W.; Senisterra, G.; Bolshan, Y.; Smil, D.; Nguyen, K. T.; Hajian, T.; Poda, G.; Al-Awar, R.; Bountra, C.; Weigelt, J.; Edwards, A. M.; Brown, P.J.; Schapira, M.; Arrowsmith, C. H.; Vedadi, M.; Wu, H.
Crystal structure of human WD repeat domain 5 with compound.
RCSB PDB 2011, PDB ID: 3SMR.

Dobrovetsky, E.; Dong, A.; Walker, J. R.; Siarheyeva, A.; Senisterra, G.; Wasney, G. A.; Smil, D.; Bolshan, Y.; Allali-Hassani, A.; Hajian, T.; Poda, G.; Bountra, C.; Weigelt, J.; Edwards, A. M.; Al-Awar, R.; Brown, P. J.; Schapira, M.; Arrowsmith, C. H.; Vedadi, M.
Crystal structure of protein arginine methyltransferase 3.
RCSB PDB 2011, PDB ID: 3SMQ.

Mottaghi, K.; Tempel, W.; Hong, B.; Smil, D.; Bolshan, Y.; Wernimont, K.; Arrowsmith, C. H.; Edwards, A. M.; Bountra, C.; Weigelt, J.; Park, H.
Human Pantothenate kinase 3 in complex with a pantothenate analog.
RCSB PDB 2011, PDB ID: 3SMS.