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Professor Blum

 

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Research Programs

Our research programs address challenges in the development of reactions for chemical synthesis. The particular focus of the laboratory involves the mechanistic and physical-organic study of reactions, producing fundamental insights that lead to the development of new reactions and the improved understanding of known reactions. To achieve this goal, we combine interdisciplinary approaches in organic, organometallic, inorganic, physical, and analytical chemistry.

Publications

44. Bel Abed, H.; Blum, S. A. “Transition Metal-Free Synthesis of Borylated Thiophenes via Formal Thioboration.” Org. Lett. ASAP DOI: 10.1021/acs.orglett.8b02727 Link

43. Tu, K. N.; Gao, C.; Blum, S. A. “An Oxyboration Route to a Single Regioisomer of Borylated Dihydrofurans and Isochromenes.” J. Org. Chem. 2018, 83 (18), 11204. Link

42. Easter, Q. T.; Blum, S. A. “Kinetics of the Same Reaction over Nine Orders of Magnitude in Concentration: When Are Unique Subensemble and Single-Turnover Reactivity Displayed?” Angew. Chem. Int. Ed. 2018, 57, 12027. Link

41. Easter, Q. T.; Blum, S. A. “Evidence for Dynamic Chemical Kinetics at Individual Molecular Ruthenium Catalysts.” Angew. Chem. Int. Ed. 2018, 57, 1572. Link

40. Issaian, A.; Tu, K. N.; Blum, S. A. “Boron Heteroatom Addition Reactions via Borylative Heterocyclization: Oxyboration, Aminoboration, and Thioboration.” Acc. Chem. Res. 2017, 50, 2598. Link

39. Easter, Q. T.; Blum, S. A. “Single Turnover at Molecular Polymerization Catalysts Reveals Spatiotemporally Resolved Reactions.” Angew. Chem. Int. Ed. 2017, 56, 13772. Link

Highlighted in Angew. Chem. Int. Ed. “Kinetics in the Real World.” Link

Highlighted in UCI News Brief, “Little green flashes unlock secrets of catalytic reactions”. Link

 

38. Issaian, A.; Faizi, D. J.; Bailey, J. O.; Mayer, P.; Berionni, G.; Singleton, D. A.; Blum, S. A. “Mechanistic Studies of Formal Thioboration Reactions of Alkynes.” J. Org. Chem. 2017, 82, 8165. Link

37. Kazuhiro, K.; Blum, S. A. "Structure–Reactivity Studies of Intermediates for Mechanistic Information by Subensemble Fluorescence Microscopy." ACS Catal20177, 3786. Link

36. Feng, C.; Easter, Q. T.; Blum, S. A. "Structure–Reactivity Studies, Characterization, and Transformation of Intermediates by Lithium Chloride in the Direct Insertion of Alkyl and Aryl Iodides to Metallic Zinc Powder." Organometallics 2017, 36, 2389. Link

Organometallics, Cover, July 2017:

35. Faizi, D. J.; Davis, A. J.; Meany, F. B.; Blum, S. A. "Catalyst-Free Formal Thioboration to Synthesize Borylated Benzothiophenes and Dihydrothiophenes." Angew. Chem. Int. Ed. 201655, 14286. Link

Highlighted in Synfacts 201713, 71. "Ring-forming Thioboration of C–C π-Bonds." Link

34. Feng, C.; Cunningham, D. W.; Easter, Q. T.; Blum, S. A. "Role of LiCl in Generating Soluble Organozinc Reagents." J. Am. Chem. Soc2016138, 11156. Link

Highlighted in Org. Process Res. Dev. 201620, 1691. "Some Items of Interest to Process R&D Chemists and Engineers." Link

33. Faizi, D. J.; Nava, N. A.; Al-Amin, M.; Blum, S. A. "Oxyboration: Synthesis of Borylated Benzofurans." Org. Synth. 201693, 228. Link

32. Johnson, J. S.; Chong, E.; Tu, K. N.; Blum, S. A. "Kinetic Study of Carbophilic Lewis Acid Catalyzed Oxyboration and the Noninnocent Role of Sodium Chloride" Organometallics 201635, 655. Link

 

31. Faizi, D. J.; Issaian, A.; Davis, A. J.; Blum, S. A. "Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration" J. Am. Chem. Soc. 2016138, 2126. Link

 

30. Hirner, J. J.; Faizi, D. J.; Blum. S. A. Organoboron Compounds and Methods of Making Organoboron Compounds. U. S. Patent 9,238661, January 19, 2016.

 

29. Tu, K. N.; Hirner, J. J.; Blum, S. A. "Oxyboration with and without a Catalyst: Borylated Isoxazoles via B–O σ-Bond Addition." Org. Lett. 201618, 480. Link

Highlighted in Synfacts 201612, 400. Link

 

 

28. Chong, E.; Blum, S. A. "Aminoboration: Addition of B–N σ Bonds Across C–C π Bonds." J. Am. Chem. Soc. 2015137, 10144. Link

27. Hirner, J. J.; Blum, S. A. "NMR Spectroscopy Studies of Electronic Effects and Equilibrium in the Organogold-to-boron Transmetallation Reaction and Studies Towards Its Application to the Alkoxyboration Addition of Boron-Oxygen Sigma-Bonds to Alkynes." Tetrahedron 201571, 4445. Special invited issue in honor of Yoshi Nakao's Tetrahedron Young Investigator AwardLink

 

26. Easter, Q. T.; Trauschke, V.; Blum, S. A." Catalyst Inefficiencies: Supported Ring-Opening Metathesis Polymerization Catalyst Yields Its Ensemble Rate from a Small Number of Molecular Active Sites." ACS Catal. 20155, 2290. Link

 

25. Al-Amin, M.; Johnson, J. S.; Blum, S. A. "Selectivity, Compatibility, Downstream Functionalization, and Silver Effect in the Gold and Palladium Dual-Catalytic Synthesis of Lactones." Organometallics 201433, 5448. Link

 

24. Hensle, E. M.; Esfandiari, N. M.; Lim, S. -G.; Blum, S. A. "BODIPY Fluorophore Toolkit for Probing Chemical Reactivity and for Tagging Reactive Functional Groups." Eur. J. Org. Chem. 2014, 3347. Link

EurJOC, Cover, June 2014 Link

 

23. Blum, S. A. "Location Change Method for Imaging Chemical Reactivity and Catalysis with Single-Molecule and -Particle Fluorescence Microscopy." Phys. Chem. Chem. Phys. 201416, 16333. Link

PCCP, Cover, August 2014 Link

 

22. Hirner, J. J.; Faizi, D. J.; Blum, S. A. "Alkoxyboration: Ring-Closing Addition of B–O Sigma Bonds Across Alkynes." J. Am. Chem. Soc. 2014136, 4740. Link

Highlighted in Science 2014344, 10. "A Big Break for Boron." Link

Organoboron building blocks for drug discovery from this paper are available from Sigma-Aldrich. Link

 

21. Al-Amin, M.; Roth, K. E.; Blum, S. A. "Mechanistic Studies of Gold and Palladium Cooperative Dual-Catalytic Cross-Coupling Systems." ACS Catal. 20144, 622. Link

 

20. Cordes, T.; Blum, S. A. "Opportunities and challenges in single-molecule and single-particle fluorescence microscopy for mechanistic studies of chemical reactions." Nat. Chem. 20135, 993. Link

 

19. Fast, A.; Esfandiari, N. M.; Blum, S. A. "Small Number of Active Sites and Single-Locus Kinetics Revealed in (salph)Co-Catalyzed Ethylene Oxide Polymerization." ACS Catal. 20133, 2150. Link

 

18. Hensle, E. M; Blum, S. A. "Phase Separation Polymerization of Dicyclopentadiene Characterized by In Operando Fluorescence Microscopy." J. Am. Chem. Soc. 2013135, 12324. Link

 

17. Hirner, J. J.; Roth, K. E.; Shi, Y.; Blum, S. A. "Mechanistic Studies of Azaphilic versus Carbophilic Activation by Gold(I) in the Gold/Palladium Dual-Catalyzed Rearrangement of Alkenyl Vinyl Aziridines." Organometallics 201231, 6843. Link

 

16. Gladysz, J. A.; Ball, Z. T.; Bertrand, G.; Blum, S. A.; Dong, V. M.; Dorta, R.; Hahn, F. E.; Humphrey, M. G.; Jones, W. D.; Klosin, J.; Manners, I.; Marks, T. J.; Mayer, J. M.; Rieger, B.; Ritter, J.; Sattelberger, A. P.; Schomaker, J. "Organometallics Roundtable 2011." Organometallics 201231, 1. Link

 

15. Cornell, T. P.; Shi, Y.; Blum, S. A. "Synthesis of Alkenylgold(I) Compounds via Sequential Hydrozirconation and Zirconium to Gold Transmetalation." Organometallics 2012, 31, 5990. Link

 

14. Esfandiari, N. M.; Blum, S. A. "Homogeneous vs Heterogeneous Polymerization Catalysis Revealed by Single-Particle Fluorescence Microscopy." J. Am. Chem. Soc. 2011133, 18145. Link

Highlighted Editor's Choice, Science 2011334, 1034. "A Probe of Homogeneity." Link

 

13. Esfandiari, N. M.; Wang, Y.; Bass, J. Y.; Blum, S. A. "Deconvoluting Subensemble Chemical Reaction Kinetics of Platinum–Sulfur Ligand Exchange Detected with Single-Molecule Fluorescence Microscopy." Inorg. Chem. 201150, 9201. Link

 

12. Roth, K. E.; Blum, S. A. "Direct Observation of Gold/Palladium Transmetalation in an Organogold Heck Reaction." Organometallics 201130, 4811. Link

 

11. Hirner, J. J.; Shi, Y.; Blum, S. A. "Organogold Reactivity with Palladium, Nickel, and Rhodium: Transmetalation, Cross-Coupling, and Dual Catalysis." Acc. Chem. Res. 201144, 603. Link

One of the "Most Read" Accounts articles

 

10. Shi, Y.; Blum, S. A. "Gold and Rhodium Transmetalation: Mechanistic Insights and Dual-Metal Reactivity." Organometallics 201130, 1776. Link

 

9. Hirner, J. J.; Blum, S. A. "Nickel-Catalyzed Cross-Coupling of Organogold Reagents." Organometallics 2011, 30, 1299. Link

 

8. Esfandiari, N. M.; Wang, Y.; Mcintire, T. M.; Blum, S. A. "Real-Time Imaging of Platinum-Sulfur Ligand Exchange Reactions at the Single-Molecule Level via a General Chemical Technique." Organometallics 201030, 2901. Link

Organometallics Cover, June 2011:

 

7. Esfandiari, N. M.; Wang, Y.; Bass, J. Y.; Cornell, T. P.; Otte, D. A. L.; Cheng, M. H.; Hemminger, J. C.; Mcintire, T. M.; Mandelshtam, V. A.; Blum, S. A. "Single-Molecule Imaging of Platinum Ligand Exchange Reaction Reveals Reactivity Distribution." J. Am. Chem. Soc. 2010132, 15167. Link

Highlighted in Chem. & Eng. News 201088 (36), 14.

Journal of the American Chemical Society Cover, November 2010:

      

 

6. Roth, K. E.; Blum, S. A. "Relative Kinetic Basicities of Organogold Compounds." Organometallics 2010, 29, 1712. Link

 

5. Shi, Y.; Roth, K. E.; Ramgren, S. D.; Blum, S. A. "Catalyzed Catalysis Using Carbophilic Lewis Acidic Gold and Lewis Basic Palladium: Synthesis of Substituted Butenolides and Isocoumarins." J. Am. Chem. Soc. 2009131, 18022. Link

 

4. Lim, S.-G.; Blum, S. A. "A General Fluorescence Resonance Energy Transfer (FRET) Method for Observation and Quantification of Organometallic Complexes under Reaction Conditions." Organometallics 200928, 4643. Link

 

3. Shi, Y.; Ramgren, S. D.; Blum, S. A. "Palladium-Catalyzed Carboauration of Alkynes and Palladium/Gold Cross-Coupling." Organometallics 200928, 1275. Link

One of the 10 "Most Read" Organometallics papers in twelve months

Highlighted in ACS-Petroleum Research Fund Feature Story, "A Synergy of Synthetic Chemistry"

 

2. Canham, S. M.; Bass, J. Y.; Navarro, O.; Lim, S. G.; Das, N.; Blum, S. A. "Toward the Single-Molecule Investigation of Organometallic Reaction Mechanisms: Single-Molecule Imaging of Fluorophore-Tagged Palladium(II) Complexes." Organometallics 200827, 2172. Link

Highlighted in Chem. & Eng. News 200886, 43.

 

1. Shi, Y.; Peterson, S. M.; Haberaecker, W. W., III; Blum, S. A. "Alkynes as Stille Reaction Pseudohalides: Synthesis of Tri- and Tetra-Substituted Olefins." J. Am. Chem. Soc. 2008130, 2168. Link

Highlighted in Angew. Chem. Int. Ed. 200847, 5703. Link