Engle, Keary M. - The Scripps Research Institute

个人简介

Education D.Phil. (Biochemistry), University of Oxford, 2013 Ph.D. (Chemistry), The Scripps Research Institute, 2013 B.S. (Chemistry, Economics, Mathematics, and Statistics), University of Michigan, 2007 Professional Experience 2013-2015 NIH Postdoctoral Research Fellow, California Institute of Technology 2007-2008 Fulbright Fellow, Max-Planck-Institut für Kohlenforschung 2008-2015 Graduate Student, Scripps Research Institute 2015-2020 Assistant Professor, Scripps Research Institute 2020-Present Professor, Scripps Research Institute 2024-Present Dean of Graduate and Postdoctoral Studies, Scripps Research Institute Awards & Professional Activities 2021 Amgen Young Investigator Award 2021 Emerging Investigator Lectureship, ChemComm 2021 NSF CAREER Award 2020 ONR Young Investigator Award 2020 Eli Lilly Organic Chemistry Award 2020 Cottrell Scholar Award 2020 Novartis Early Career Award in Organic Chemistry 2019 Alfred P. Sloan Fellowship 2019 Boehringer Ingelheim Scientific Advancement Grant 2019 Camille Dreyfus Teacher-Scholar Award 2018 ACS Petroleum Research Fund Doctoral New Investigator Grant 2018 Bristol-Myers Squibb Unrestricted Grant 2018 Bayer Early Excellence in Science Award 2017 TSRI Society of Fellows Outstanding Mentor 2017 Thieme Chemistry Journal Award 2016 Donald E. and Delia B. Baxter Foundation Young Faculty Award 2014 IUPAC-Solvay International Award for Young Chemists 2013 Ruth L. Kirschstein National Research Service Award (NIH F32) 2012 Kenneth G. Hancock Memorial Student Award, ACS Green Chemistry Institute 2011 K. Patricia Cross Future Leaders Award, American Association of Colleges and Universities 2008 Skaggs-Oxford Scholarship, Scripps Research Institute and Oxford University 2008 NSF Graduate Research Fellowship, National Science Foundation 2008 National Defense Science and Engineering Graduate Fellowship, ASEE 2007 J. William Fulbright Scholarship, International Institute of Education

研究领域

Organic small molecules make up the vast majority of medicines, biological probes, agrochemicals, and materials building blocks. Thus, though they are ubiquitous in modern society, many classes of small molecules remain problematic to prepare using conventional methods. Contemporary synthetic routes routinely require multiple steps, generate large quantities of waste, or require substantial human energy to troubleshoot. Research in the Engle group focuses on addressing these challenges by harnessing the power of catalysis. Our group's goal is to advance the efficiency, effectiveness, and sustainability of chemical synthesis. The projects that we tackle are highly interdisciplinary, and as a consequence, students complement their core training in synthetic organic, physical organic, and organometallic chemistry with expertise in related disciplines in and outside of chemistry.

近期论文

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Pessemesse, Q.; Mendoza, S. D.; Peltier, J. L.; Gojiashvili, E.; Ravn, A. K.; Lorkowski, J.; Gembicky, M.; Bera, S. S.; Payard, P.-A.; Engle, K. M.; Jazzar, R. “Harnessing Multi-Center-2-Electron Bonds for Carbene Metal–Hydride Nanocluster Catalysis,” ChemRxiv 2024, DOI: 10.26434/chemrxiv-2024-0nz99. (†Authors contributed equally) Yang, S.; Deng, M.; Daley, R. A.; Darù, A.; Wolf, W. J.; George, D. T.; Ma, S.; Werley, B. K.; Samolova, E.; Bailey, J. B.; Gembicky M.; Marshall, J.; Wisniewski, S. R.; Blackmond D. G.; Engle, K. M. “Palladium Bisphosphine Mono-Oxide Complexes: Synthesis, Scope, Mechanism, and Catalytic Relevance,” ChemRxiv 2024, DOI: 10.26434/chemrxiv-2024-8qcg4. He, W.-J.; Qin, W.-Z.; Yang, S.; Ma, S.; Kim, N.; Schultz, J. E.; Palkowitz, M. D.; He, C.; Ma, A.; Schmidt, M. A.; Gembicky, M.; Wisniewski, S. R.; Engle, K. M. ” Pd(COD)(DQ): A Stable, Versatile, and Monometallic Palladium(0) Source for Organometallic Synthesis and Catalysis,” ChemRxiv 2024, DOI: 10.26434/chemrxiv-2024-sj081. Sun, J.; Hu, Y.; Liao, C.-X.; He, W.-J.; Wong, Q. N.; Engle, K. M. “Dual Catalytic C(sp2)–H Activation of Azaheterocycles towards C– N Atropisomers,” ChemRxiv 2023, DOI: 10.26434/chemrxiv-2023-nlvw0. Jankins, T. C.; Rubel, C. Z.; Ho, H. C.; Martin-Montero, R.; Engle, K. M. “A Unified Approach to (E)- and (Z)-Olefins Enabled by Low-Valent Tungsten Catalysis,” ChemRxiv 2023, DOI: 10.26434/chemrxiv-2023-hdj6t. He, W.-J.; Lisboa, A. V. R. D.; Engle, K. M. “Duroquinone,” e-EROS 2024, In Press. Li, Z.-Q.; Alturaifi, T. M.; Cao, Y.; Joannou, M. V.; Liu, P.; Engle, K. M. “Hemilabile and Redox-Active Quinone Ligands Unlock sp3-Rich Couplings in Nickel-Catalyzed Olefin Carbosulfenylation,” Angew. Chem. Int. Ed. 2024, 63, e202411870. Ni, H.-Q.; Rodphon, W.; Scherschel. N. F.; Yang, S.; Wang, F.; McAlpine, I. J.; Piercey, D. G.; Engle, K. M. “Anti-Selective Cyclopropanation of Non-Conjugated Alkenes with Diverse Pronucleophiles via Directed Nucleopalladation,” J. Am. Chem. Soc. 2024, 146, 24503–24514. Tran, V. T.†; Ravn, A. K.†; Rubel, C. Z.†; Xu, M.†; Fu, Y.†; Wagner, E. M.; Wisniewski, S. R.; Liu, P.; Gutekunst, W. R.; Engle, K. M. “Ni-Catalyzed Dicarbofunctionalization for the Synthesis of Sequence-Encoded Cyclooctene Monomers,” Nat. Synth. 2024, DOI: 10.1038/s44160-024-00618-1. (†Authors contributed equally) Zhao, H.; Ravn, A. K.; Haibach, M. C.; Engle, K. M.; Johansson Seechurn, C. C. C. C. “The Diversification of Pharmaceutical Manufacturing Processes: Taking the Plunge into the Non-PGM Catalysis Pool,” ACS Catal. 2024, 14, 9708–9733. Rubel, C. Z.†; Ravn, A. K.†; Ho, H. C.; Yang, S.; Li, Z.-Q.; Engle, K. M.; Vantourout, J. C. “Stereodiverent, Kinetically Controlled Isomerization of Terminal Alkenes via Nickel Catalysis,”Angew. Chem. 2024, 136, e202320081; Angew. Chem. Int. Ed. 2024, 63, e202320081. (†Authors contributed equally) Laudadio, G.; Neigenfind, P.; Péter, A.; Rubel, C. Z.; Emmanuel, M. A.; Oderinde, M. S.; El-Hayek Ewing, T.; Palkowitz, M. D.; Sloane, J. L.; Gillman, K. W.; Ridge, D.; Mandler, M. D.; Bolduc, P.; Nicastri, M.; Zhang, B.; Clementson, S.; Peterson, N. N.; Martín-Gago, P; Mykhailiuk, P.; Engle, K. M.; Baran P. S. “Ni-Electrocatalytic Decarboxylative Arylation to Access Quaternary Centers,” Angew. Chem. 2024, 136, e202314617; Angew. Chem. Int. Ed. 2024, 63, e202314617. Rubel, C. Z.; He, W.-J.; Wisniewski, S. R.; Engle, K. M. “Benchtop Nickel Catalysis Invigorated by Electron-Deficient Diene Ligands,” Acc. Chem. Res. 2024, 57, 312–326. Kang, T.; Apolinar, O.; Engle, K. M.; “Ni- and Pd-Catalyzed Enantioselective 1,2-Dicarbofunctionalization of Alkenes,” Synthesis 2024, 1, 1–15. Rubel, C. Z.; Cao, Y.; El-Hayek Ewing, T.; Laudadio, G.; Beutner, G.; Wu, X.; Wisniewski, S. R.; Baran, P. S.; Vantourout, J. C.; Engle, K. M. “Electroreductive Synthesis of Ni(0) Complexes,” Angew. Chem. 2024, 136, e202311557; Angew. Chem. Int. Ed. 2024, 63, e202311557. Hwang, Y.; Wisniewski, S. R.; Engle, K. M. “Ligand-Enabled Carboamidation of Unactivated Alkenes through Enhanced Organonickel Electrophilicity,” J. Am. Chem. Soc. 2023, 145, 25293–25303. Cao, Y.; Li, Z.-Q.; Engle, K. M. “Ni-Catalyzed 1,2-Diarylation of Unactivated Alkenes Directed by Diverse Azaheterocycles,” Tetrahedron Lett. 2023, 132, 154764. Ni, H.-Q.; Dai, J.-C.; Yang, S.; Loach, R. P.; Chuba, M. D.; McAlpine, I. J.; Engle, K. M. “Catalytic σ-Bond Annulation with Ambiphilic Organohalides Enabled by β-X Elimination,” Angew. Chem. 2023, 136, e202306581; Angew. Chem. Int. Ed. 2023, 62, e202306581. Ni, H.-Q.; Karunananda, M. K.; Zeng, T.; Yang, S.; Liu, Z.; Houk, K. N.; Liu, P.; Engle, K. M. “Redox-Paired Alkene Difunctionalization Enables Skeletally Divergent Synthesis,” J. Am. Chem. Soc. 2023, 145, 12351–12359. Simlandy, A. K.; Alturaifi, T. M.; Nguyen, J. M.; Oxtoby, L. J.; Wong, Q. N.; Chen, J. S.; Liu, P.; Engle, K. M. “Enantioselective Hydroalkenylation and Hydroalkynylation of Alkenes Enabled by a Transient Directing Group: Catalyst Generality through Rigidification,” Angew. Chem. 2023, 135, e202304013; Angew. Chem. Int. Ed. 2023, 62, e202304013. Chirik, P. J.; Engle, K. M.; Simmons, E. M.; Wisniewski, S. R. “Collaboration as a Key to Advance Capabilities for Earth-Abundant Metal Catalysis,” Org. Process Res. Dev. 2023, 27, 1160–1184. Zhang, T.; Zhong, K.; Lin, Z.-K.; Niu, L.; Li, Z.-Q.; Bai, R.; Engle, K. M., Lan, Y. “Revised Mechanism of C(sp3)–C(sp3) Reductive Elimination from Ni(II) with the Assistance of a Z-Type Metalloligand,” J. Am. Chem. Soc. 2023, 145, 2207–2218.TOC-revised Tran, V. T.†; Kim, N.†; Rubel, C. Z.; Wu, X.; Kang, T.; Jankins, T. C.; Li, Z.-Q.; Joannou, M. V.; Ayers, S.; Gembicky, M.; Bailey, J.; Sturgell, E. J.; Sanchez, B. B.; Chen, J. S.; Lin, S.; Eastgate, M. D.; Wisniewski, S. R.; Engle, K. M. “Structurally Diverse Bench-Stable Nickel(0) Pre-Catalysts: A Practical Toolkit for In Situ Ligation Protocols,” Angew. Chem. 2023, 135, e202211794; Angew. Chem. Int. Ed. 2023, 62, e202211794. (†Authors contributed equally) Kang, T.; Fu, Y.; Matsuura, R.; Liu, A. L.; Jankins, T. C.; Rheingold, A. L.; Bailey, J. B.; Gembicky, M.; Liu, P.; Engle, K. M. “Synthesis and Characterization of Post-β-Carbon-Elimination Organopalladium Complexes,” Organometallics 2023, 42, 11–15. Liu, Z.; Oxtoby, L. J.; Sun, J.; Li, Z.-Q.; Kim, N.; Davies, G. H. M.; Engle, K. M. “A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2-Carbofluorination of Alkenyl Carbonyl Compounds,” Angew. Chem. 2023, 135, e202214153; Angew. Chem. Int. Ed. 2023, 62, e202214153. Simlandy, A. K.; Rodphon, W.; Alturaifi, T. M.; Mai, B. K.; Ni, H.-Q.; Gurak, J. A., Jr.; Liu, P.; Engle, K. M. “Catalytic Addition of Nitroalkanes to Unactivated Alkenes via Directed Carbopalladation,” ACS Catal. 2022, 12, 13755–13762. Apolinar, O.†; Kang, T.†; Alturaifi, T. M.; Bedekar, P. G.; Rubel, C. Z.; Derosa, J.; Sanchez, B. B.; Wong, Q. N.; Sturgell, E. J.; Chen, J. S.; Wisniewski, S. R.; Liu, P.; Engle, K. M. “Three-Component Asymmetric Ni-Catalyzed 1,2-Dicarbofunctionalization of Unactivated Alkenes via Stereoselective Migratory Insertion,” J. Am. Chem. Soc. 2022, 144, 19337–19343. (†Authors contributed equally) Liu, M.; Sun, J.†; Zhang, T.†; Ding, Y.; Han, Y.-Q.; Martín-Montero, R.; Lan, Y.; Shi, B.-F.; Engle, K. M. “Regio- and Stereoselective 1,2-Oxyhalogenation of Non-Conjugated Alkynes via Directed Nucleopalladation: Catalytic Access to Tetrasubstituted Alkenes,” Angew. Chem. 2022, 134, e202209099; Angew. Chem. Int. Ed. 2022, 61, e202209099. (†Authors contributed equally) Rubel, C. Z.; Kim, N.; Engle, K. M. “(1,5-Cyclooctadiene)(tetramethyl-p-benzoquinone)nickel,” e-EROS 2022, DOI: 10.1002/047084289X.rn02446. Jankins, T. C.; Bell, W. C.; Zhang, Y.; Qin, Z-.Y.; Gembicky, M.; Chen, J. S.; Liu, P.; Engle, K. M. “Low-Valent Tungsten Redox Catalysis Enables Controlled Isomerization and Cabonylative Functionalization of Alkenes,” Nat. Chem. 2022, 14, 632–639 Gao, Y.; Kim, N.;† Mendoza, S. D.†; Yazdani, S.; Liu, M.; Kendrick, A., IV, Grotjahn, D. B.; Bertrand, G.; Jazzar, R.; Engle, K. M. “(CAAC)Copper Catalysis Enables Regioselective Three-Component Carboboration of Terminal Alkynes,” ACS Catal. 2022, 12, 7243–7247. (†Authors contributed equally). Li, Z.-Q.; He, W.-J.; Ni, H.-Q.; Engle, K. M. “Directed, Nickel-Catalyzed 1,2-Alkylsulfenylation of Alkenyl Carbonyl Compounds,” Chem. Sci. 2022, 13, 6567–6572. Liu, M.; Sun, J.; Erbay, T.; Ni, H.-Q.; Martín-Montero, R.; Liu, P.; Engle, K. M. “Pd(II)-Catalyzed C(alkenyl)–H Activation Facilitated by a Transient Directing Group,” Angew. Chem. Int. Ed. 2022, 61, e202203624, Angew. Chem. 2022, 134, e202203624. Li, Z.-Q.; Cao, Y.; Kang, T.; Engle, K. M. “Electrophilic Sulfur Reagent Design Enables Directed syn-Carbosulfenylation of Unactivated Alkenes,” J. Am. Chem. Soc. 2022, 144, 7189–7197. Kang, T.; González, J. M.; Li, Z.-Q.; Foo, K.; Cheng, P. T. W.; Engle, K. M. “Alkene Difunctionalization Directed by Free Amines: Diamine Synthesis via Nickel-Catalyzed 1,2-Carboamination,” ACS Catal 2022, 12, 3890–3896. Ni, H.-Q.; Cooper, P. Yang, S.; Wang, F.; Sach, N.; Bedekar, P. G.; Donaldson, J. S.; Tran-Dubé, McAlpine, I. J.; Engle, K. M. “Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-conjugated Alkenes via Pd(II)/Pd(IV) Catalysis,” Angew. Chem. 2022, 134, e202114346; Angew. Chem. Int. Ed. 2022, 61, e202114346. Liu, M.; Sun, J.; Engle, K. M. “Recent Advances in the Generation and Functionalization of C(alkenyl)–Pd Species for Catalytic Polysubstituted Alkene Synthesis,” Tetrahedron 2022, 103, 132513. Liu, B.†; Romine, A. M.†; Rubel, C. Z; Engle, K. M.; Shi, B.-F. “Coordination-Assisted, Transition-Metal-Catalyzed Functionalization of Nonactivated C(sp3)–H Bonds.” Chem. Rev. 2021, 121, 14957–15074. (†Authors contributed equally) Jankins, T. C.†; Martin-Montero, R.†; Cooper, P.; Martin, R.; Engle, K. M. “Low-Valent Tungsten Catalysis Enables Site-Selective Isomerization–Hydroboration of Unactivated Alkenes,” J. Am. Chem. Soc. 2021, 143, 14981–14986. (†Authors contributed equally) Kang, T.; Kim, N.; Cheng, P. T.; Zhang, H.; Foo, K.; Engle, K. M. “Nickel-Catalyzed 1,2-Carboamination of Alkenyl Alcohols,” J. Am. Chem. Soc. 2021, 143, 13962–13970. Li, Z.-Q.; Apolinar, O.; Deng, R.; Engle, K. M. “Directed Markovnikov Hydroarylation and Hydroalkenylation of Alkenes Under Nickel Catalysis,” Chem. Sci. 2021, 12, 11038–11044. Ni, H.-Q.†; Cooper, P.†; Engle, K. M. “Recent Advances in Palladium-Catalyzed (Hetero)annulation of C=C Bonds with Ambiphilic Aryl (Pseudo)halides,” Chem. Commun. 2021, 57, 7610–7624.(†Authors contributed equally) Gao, Y.; Yazdani, S.; Kendrick, A., IV; Junor, G. P.; Kang, T.; Grotjahn, D. B.; Bertrand, G.; Jazzar, R.; Engle, K. M. “Cyclic(Alkyl)(Amino)Carbene Ligands Enable Cu-Catalyzed Markovnikov Protoborylation and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes,” Angew. Chem. Int. Ed. 2021, 60, 19871–19878; Angew. Chem. 2021, 133, 20024–20031. Kleinmans, R.†; Apolinar, O.†; Derosa, J.; Karunananda, M. K.; Li, Z.-Q.; Tran, V. T.; Wisniewski, S. R.; Engle, K. M. “Nickel-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems,” Org. Lett. 2021, 23, 5311–5316. (†Authors contributed equally) Ni, H.-Q.; Li, Z.-Q.; Tran, V. T.; Engle, K. M. “Modular Synthesis of Non-Conjugated N-(Quinolin-8-yl) Alkenyl Amides via Cross-Metathesis,” Tetrahedron 2021, 93, 132279. Liu, Z.; Oxtoby, L. J.; Liu, M.; Li, Z.-Q.; Tran, V. T.; Gao, Y.; Engle, K. M. “A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis,” J. Am. Chem. Soc. 2021, 143, 8962–8969. Romine, A. M.; Demer, M. J.; Gembicky, M.; Rheingold, A. L.; Engle, K. M. “Ligand Rearrangement Leads to Tetrahydrothiophene-Functionalized N,S-Heterocyclic Carbene Palladium(II) Complexes,” Organometallics 2021, 40, 2311–2319. Matsuura, R.; Karunananda, M. K.; Liu, M.; Nguyen, N.; Blackmond, D. G.; Engle, K. M. “Mechanistic Studies of Pd(II)-Catalyzed E/Z Isomerization of Unactivated Alkenes: Evidence for a Monometallic Nucleopalladation Pathway,” ACS Catal. 2021, 11, 4239–4246.