Faculty - James R. Green

AWARDS AND DISTINCTIONS:

2004 - Alumni Award for Distinguished Contributions to University Teaching

RESEARCH INTERESTS:

Our research interests lie in the synthetic organic chemistry that employs organometallic complexes, including catalysis involving organometallic compounds. The goals are in the development of novel organic reactions to give types of compounds not easily accessible by other methods, and the application of these transformations in organic synthesis. In particular, we are actively engaged in the application of the chemistry of alkyne-Co2(CO)6 complexes, and the use of propargyl cations and allylic cations, to make advances in several areas, including:

• New routes medium-sized ring synthesis: We are in the continuing process of developing the chemistry of Co2(CO)6 complexes of cycloheptynes and cyclooctynes into methods that can result in the preparation of important compounds containing seven- and eight- membered ring systems. Novel syntheses of anticancer allocolchicines and schizandrins, and rearranged abietane compounds that have served as folk remedies are examples of synthetic targets based on this chemistry. Catalytic methods for construction of these ring systems are also under investigation. Several of the intermediate molecules, such as dehydrotropylium ion-Co2(CO)6 cation, are of theoretical interest simply from their existence, and aspects of their stability are also under investigation.
   
• γ-Carbonyl cations in organic synthesis: We are pursuing novel methods of allylating and/or propargylating electron rich compounds, with a focus in the creation of γ-carbonyl cation equivalents. These methods include both intermediate cations stabilized by a Co2(CO)6 unit and by employing catalytic methods. Within this area we are both targeting the synthesis naturally occurring terpenoid compounds with biological activity (i.e., microstegiol), and an understanding of the details of the fundamental reactivity of the electrophilic intermediates.

SELECTED PUBLICATIONS:

• Almubayedh, S.; Green, J. R.* (2022) Alkynedicobalt Mediated Vinylogous Nazarov Reactions, Org. Biomol. Chem., 20, 1004-1007.
• Potter, M.; Green, J.; Mutus, B.* (2022) Fluorescein Isothiocyanate, a Platform for the Selective and Sensitive Detection of S-Nitrosothiols and Hydrogen Sulfide, Talanta, 237, 122981 (1-7).
• St. Onge, B.; Taimoory, S. M.; Battersby, J.; Trant, J. F.*, Green, J. R.* (2021) Reaction of Alkynyl- and Alkenyltrifluoroborates with Propargyldicobalt Cations. Alkynylation, Alkenylation and Cyclopropanation Product Pathways, J. Org. Chem., 86, 18094-18106.
• St. Onge, B.; Green, J. R.* (2021) The Formation of Benzoxacin-3-ones via Intramolecular Nicholas Reactions and Synthesis of 8-Membered Heliannuols, Org. Biomol. Chem., 19, 7152-7155.
• Muresan, M.; Subramanian, H.; Sibi, M. P.*; Green, J. R.* (2021) Propargyl Radicals in Organic Synthesis, Eur. J. Org. Chem., 3359-3375.
• Green, J. R.*; Nicholas, K. M.* (2020) Propargyl Coupling Reactions via Bimetallic Alkyne Complexes: the Nicholas Reaction, Org. React., 103, 931-1324.
• Kaczmarek, R.; Korczyński, D.; Green, J. R.^*; Dembinski, R.^* (2020) Extension of the 5-Alkynyluridine Side Chain via C–C-Bond Formation in Modified Organometallic Nucleosides Using the Nicholas Reaction, Beilstein J. Org. Chem., 16, 1-8.
• Mehdi, M. A.; Bushnell, E. A. C.; Nikoo, S.; Gauld, J. W.; Green, J. R.* (2019) Generation and Reactions of a Benzodehydrotropylium ion-Co₂(CO)₆ Complex, ACS Omega, 4, 18600-18608.
• St. Onge, B.; Green, J. R.*(2017) Nicholas Reactions of Alkynyl- and Alkenyltrifluoroborates, Synlett, 28, 2923-2928. (invited)
• Green, J. R.*; Mehdi, M.; Djurdjevic, S. (2017) “Catalytic Method for Dibenzocycloheptane Synthesis and Allocolchicinoid Synthesis” USA patent No. 9,573,873, Feb 21, 2017.
• Tang,A.; Bell, J. G.; Green, J. R.;* Wang, J.* (2017) Complex Nonlinear Behavior in the Bromate - 2-Aminophenol Reaction, Int. J. Chem. Kinet., 49, 21-27.
• Mahmood, A.; Ngenzi, R.; Penner, P. M.; Green, J. R.* (2016) Remote Functionalization in Nicholas Reactions of Vinylogous γ-Carbonyl Cations, Synlett, 27, 1245-1250.
• Kolodziej, I.; Green, J. R.* (2015) Vinylogous Nicholas Reactions in the Synthesis of Bi- and Tricyclic Cycloheptynedicobalt Complexes, Org. Biomol. Chem., 13, 10852-10864.
• Mehdi, M.; Djurdjevic, S.; Green, J. R.* (2015) “Lewis Acid Catalyzed Synthesis of Allocolchicinoids” Synlett, 26, 2408-2412.
• Djurdjevic, S.; Green, J. R.* (2014) “Synthesis of Tenuifolin via Intramolecular Nicholas Reaction”, Synlett, 25, 2467-2470.
• Larocque, K.; Ovadje, P.; Djurdjevic, S.; Mehdi, M.; Green, J.; Pandey, S.* (2014) "Novel Analogue of Colchicine Induces Selective Pro-Death Autophagy and Necrosis in Human Cancer Cells", PLoS ONE, 9:e87064.   
• Djurdjevic, S.; Green, J. R.* (2013) "Nicholas Reaction in the Synthesis of Dicobalt Dibenzocyclooctyne Complexes" Org. Lett., 15, 5468-5471.
• Henkie, J. R.; Dhaliwal, S.; Green, J. R* (2012) “Bicatalytic Allylation-Cross Metathesis Reactions as γ-Carbonyl Cation Equivalents” Synlett, 23, 2371-2374.
• Green, J. R* (2012) “Alkynedicobalt Complexes in γ-Carbonyl Cations and Cycloheptynedicobalt Complexes” Synlett, 23, 1271-1282, Invited Account.
• Amiralaei, S.; Gauld, J.; Green, J. R.* (2011) “Dehydrotropylium-Co2(CO)6 Ion. Generation, Reactivity and Evaluation of Cation Stability”, Chem. Eur. J., 11, 4157-4165.

 

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