Michael, Forrest E. - University of Washington

个人简介

EDUCATION Harvard University 1995-2001 Ph.D. in Chemistry, 2001; A.M. in Chemistry, 1998 Thesis: Chiral Mixed Phosphorus/Sulfur Ligands in Late Transition Metal Catalyzed Reactions:Structure, Reactivity, and Mechanism The Pennsylvania State University (University Scholars Program) 1991-1995 B.S. in Chemistry, B.S. in Mathematics, Minor in German, 1995 Graduated with Distinction and with Honors in Chemistry RESEARCH EXPERIENCE Associate Professor of Chemistry 2010-present Assistant Professor of Chemistry 2004-2010 University of Washington, Seattle, WA Developing new catalytic methods for the construction of molecules with a focus on C-N bond construction. Conducting mechanistic studies of metal-catalyzed and organocatalyzed reactions

研究领域

The Michael group is interested in understanding the fundamental mechanisms of organic and organometallic reactions and applying those mechanisms to the development of new catalytic methods for the construction of organic compounds. We use the tools of physical organic chemistry to understand unusual reactivity and modes of selectivity. Simultaneously, we use the mechanistic information gleaned from such studies to design new catalytic reactions that address unsolved problems in C-N and C-C bond formation. Our current areas of interest are Developing strategies to control and inhibit beta-hydride elimination in transition metal complexes, with a particular focus on C-N bond forming reactions. Understanding the principles behind successful stereocontrol in enantioselective reactions. Harnessing hypervalent main group chemistry (e.g. iodine(III), selenium(IV)) to activate and functionalize C-C multiple bonds. New strategies for the selective activation of C-H bonds.

近期论文

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Teh, W. P.; Obenschain, D. C.; Black, B. M., Michael, F. E. "Catalytic Metal-free Allylic C-H Amination of Terpenoids” J. Am. Chem. Soc. 2020, 142(39), 16717-16722. DOI: 10.1021/jacs.0c06997 Tabor, J. R.; Obenschain, D. C.; Michael, F. E. "Selenophosphoramide-Catalyzed Diamination and Oxyamination of Alkenes” Chem. Sci. 2020, 11, 1677-1682. DOI: 10.1039/C9SC05335B Zheng, T.; Tabor, J. R.; Stein, Z. L.; Michael, F. E. “Regioselective Metal-Free Aza-Heck Reactions of Terminal Alkenes Catalyzed by Phosphine Selenides” Org. Lett. 2018, 20, 6975-6978. DOI: 10.1021/acs.orglett.8b03159 Teh, W. P.; Michael, F. E. “Palladium-Catalyzed Cross-Coupling of N-Sulfonylaziridines and Alkenylboronic Acids: Stereospecific Synthesis of Homoallylic Amines with Di-and Trisubstituted Alkenes” Org. Lett. 2017, 19, 1738-1740. DOI: 10.1021/acs.orglett.7b00504 Ingalls, E. L.; Holtzen, G. A.; Kaminsky, W.; Michael, F. E. “Synthesis and Structural Characterization of Palladium(II) Complexes of Chiral Bidentate N-Heterocyclic Carbene-Quinoline Ligands” J. Organomet. Chem. 2017, 832, 9-11. DOI: 10.1016/j.jorganchem.2017.01.008 Rosewall, C. F.; Ingalls, E. L.; Kaminsky, W.; Michael, F. E. “Chelation-driven Rearrangement of Primary Alkyl Aminopalladation Products to Stable Trisubstituted Alkyl Palladium Complexes” Angew. Chem. Int. Ed. 2015, 54, 4557-4560. DOI: 10.1002/anie.201412033 Duda, M. L.; Michael, F. E. “Palladium-Catalyzed Cross-Coupling of N-Sulfonylaziridines with Boronic Acids” J. Am. Chem. Soc. 2013, 135, 18347-18349. DOI: 10.1021/ja410686v Pierson, J.; Ingalls, E. L.; Vo, R.; Michael, F. E. “Palladium(II)-Catalyzed Intramolecular Hydroamination of 1,3-Dienes to Give Homoallylic Amines” Angew. Chem. Int. Ed. 2013, 52, 13311-13313. DOI: 10.1002/anie.201305766 McGhee, A.; Cochran, B. M.; Stenmark, T.; Michael F. E. “Stereoselective synthesis of 2,5-disubstituted morpholines using a palladium-catalyzed hydroamination reaction” Chem. Comm. 2013, 49, 6800-6802. DOI: 10.1039/C3CC44117B Ingalls, E. L.; Sibbald, P. A.; Kaminsky, W.; Michael, F. E. “Enantioselective Palladium-Catalyzed Diamination of Alkenes Using N-Fluorobenzenesulfonamide” J. Am. Chem. Soc. 2013, 135, 8854-8856. DOI: 10.1021/ja4043406 Okamoto, K.; Housekeeper, J. B.; Michael, F. E.; Luscombe, C. K. “Thiophene based hyperbranched polymers with tunable branching using direct arylation methods” Polym. Chem. 2013, 4, 3499-3506. DOI: 10.1039/C3PY00412K Bjelic, S.; Nivon, L. G.; Celebi-Olcum, N.; Kiss, G.; Rosewall, C. F.; Lovick, H. M.; Ingalls, E. L.; Gallaher, J. L.; Seetharaman, J.; Lew, S.; Montelione, G. T.; Hunt, J. F.; Michael, F. E.; Houk, K. N.; Baker, D. “Computational Design of Enone-Binding Proteins with Catalytic Activity for the Morita-Baylis-Hillman Reaction” ACS Chemical Biology 2013, 8, 749-757. DOI: 10.1021/cb3006227 Liskin, D. V.; Sibbald, P. A.; Rosewall, C. F.; Michael, F. E. “Palladium Catalyzed Alkoxyamination of Alkenes with Use of N-Fluorobenzenesulfonimide as Oxidant.” J. Org. Chem. 2010, 75, 6294–6296. DOI: 10.1021/jo101171g Siegel, J. B.; Zanghellini, A.; Lovick, H. M.; Kiss, G.; Lambert, A. R.; St.Clair, J. L.; Gallaher, J. L.; Hilvert, D.; Gelb, M. H.; Stoddard, B.; Houk, K. N.; Michael, F. E.; Baker, D. “Computational design of an enzyme catalyst for a stereoselective bimolecular Diels-Alder reaction.” Science 2010, 329, 309–313. DOI: 10.1126/science.1190239 Hoover, J. M.; DiPasquale, A.; Mayer, J. M.; Michael, F. E. “Platinum Catalyzed Intramolecular Hydrohydrazination: Evidence for Alkene Insertion into a Pt-N Bond.” J. Am. Chem. Soc. 2010, 132, 5043–5053. DOI: 10.1021/ja906563z Lovick, H. M.; Michael, F. E. “Metal-Free Highly Regioselective Aminotrifluoroacetoxylation of Alkenes.” J. Am. Chem. Soc. 2010, 132, 1249–1251. DOI: 10.1021/ja906648w Sibbald, P. A.; Rosewall, C. F.; Swartz, R. D.; Michael, F. E. “Mechanism of N-Fluorobenzenesulfonimide Promoted Diamination and Carboamination Reactions: Divergent Reactivity of a Pd(IV) Species.” J. Am. Chem. Soc. 2009, 131, 15945–15951. DOI: 10.1021/ja906915w Rosewall, C. F.; Sibbald, P. A.; Liskin, D. V.; Michael, F. E. “Palladium Catalyzed Carboamination of Alkenes Promoted by N-Fluorobenzenesulfonimide via C-H Activation of Arenes.” J. Am. Chem. Soc. 2009, 131, 9488–9489. DOI: 10.1021/ja9031659 Sibbald, P. A.; Michael, F. E. “Palladium-Catalyzed Diamination of Unactivated Alkenes Using N-fluorobenzenesulfonimide as a Source of Electrophilic Nitrogen.” Org. Lett. 2009, 11, 1147–1149. DOI: 10.1021/ol9000087 Lovick, H. M.; Michael F. E. “Reversal of enantioselectivity using tethered bisguanidine catalysts in the aza-Henry reaction.” Tetrahedron Lett. 2009, 50, 1016–1019. DOI: 10.1016/j.tetlet.2008.12.058