个人简介
Boston College B.S. with Honors, 2006 Advisor: Scott J. Miller
Princeton University Ph.D. in Chemistry, 2011 Advisor: David W.C. MacMillan
University of California, Berkeley NIH Postdoctoral Fellow, 2014 Advisor: F. Dean Toste
avid grew up near Philadelphia, PA as the eldest of four siblings in an Egyptian family with a strong love for teaching and education. In 2006, he earned a B.S. in Chemistry at Boston College, where he was awarded the university’s Scholar of the College prize for his thesis work with Prof. Scott Miller entailing the synthesis of small peptide catalysts that mimic enzymes to desymmetrize meso-diols. In 2011, he earned his Ph.D. with Prof. David MacMillan at Princeton University, developing several new trifluoromethylation reactions by pioneering catalytic strategies for the mild generation of CF3 radicals. During his graduate studies, David was the first to employ an Ir photocatalyst in organic synthesis, and he combined it with organocatalytic activation to develop the first catalytic, enantioselective trifluoromethylation of carbonyls. He also applied this radical strategy to the synthesis of medicinally important organofluorines via C-H functionalization of medicines such as lipitor and ibuprofen. As a Ruth L. Kirschstein NIH Postdoctoral Scholar with Prof. F. Dean Toste at the University of California, Berkeley, David continued developing new C-H activation strategies by harnessing selective, oxidative gold mechanisms to enable unique C-C and C-N bond-forming reactivity. In collaboration with Prof. Omar Yaghi, he also illustrated the catalytic utility of post-synthetically modified MOF (metal-organic framework) materials as size-specific heterogeneous catalyst architectures.
研究领域
The Nagib Laboratory seeks to bridge the gap between what is possible and practical in the realm of organic synthesis. Our goal is to expand the synthetic toolbox by designing fundamentally new activation strategies and catalysts. We aim to harness the untapped reactivity of cheap and abundant chemical feedstocks as well as enable the late-stage functionalization of complex natural products. We are currently inventing multi-faceted approaches for selective C-H and C-O activation, using combinations of radical (1e-) and closed shell (2e-) processes. By emphasizing the design of novel, dual-catalytic strategies (organometallic, organocatalytic, redox-neutral, etc.) and a careful elucidation of their unique mechanisms, we are developing useful methodologies to enable non-classical synthetic disconnections. Our chemistry has important applications in various interdisciplinary arenas, including the streamlined synthesis of improved medicines, materials, and biofuels.
Harnessing Radicals
The frequent need for harsh chemical or photolytic conditions to generate radicals has created the misconception that radical chemistry is incompatible with complex organic synthesis. Our lab is developing new techniques for mild generation of open shell intermediates in order to demonstrate that radical reactivity can be harnessed as an important tool to enable useful synthetic disconnections that are either complementary (umpolung) with, or difficult to achieve (C-H activation) by, two-electron processes.
C-H Activation
Recent innovations in organometallic and radical-based C-H activation strategies have demonstrated that this most ubiquitous (non)functional group can be exploited to introduce synthetic complexity to simple molecules in a more direct and efficient manner. Our lab is building on the rare and exciting examples of selective C-H functionalization by developing a toolbox of catalysts that can introduce new functional groups at any desired position of a simple or complex molecule. By replacing substrate-based selectivity with catalyst-directed programming, classic retrosynthetic analysis can be complemented by at-will functionalization of late-stage synthetic intermediates as well as biologically-derived natural products.
C-O Activation
While cleavage of a C-O bond is one of the most common retrosynthetic disconnections in organic synthesis (e.g. Mitsunobu displacement of alcohols, peptide coupling of carboxylic acids), there is a significant dearth in catalytic strategies to displace an -OH group – forcing chemists to rely on wasteful, stoichiometric activation before desired C-O displacement. Our lab is designing captodative catalysts (with synergistic push-pull electronics) to enable the thermodynamically favorable displacement of H2O as a sole, environmentally-friendly byproduct. This approach enables catalytic access to some of the most frequently employed and valuable transformations in organic synthesis.
近期论文
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Carbene reactivity from alkyl and aryl aldehydes Lumin Zhang, Bethany M. DeMuynck †, Alyson N. Paneque †, Joy E. Rutherford †, and David A. Nagib Science, 2022, 377, 649–654
γ C–H Functionalization of Amines via Triple H-Atom Transfer of a Vinyl Sulfonyl Radical Chaperone James H. Herbort †, Taylor N. Bednar †, Andrew D. Chen, T. V. RajanBabu, and David A. Nagib J. Am. Chem. Soc., 2022, 144, 13366–13373
Radical Aza-Heck Cyclization of Imidates via Energy Transfer, Electron Transfer, and Cobalt Catalysis Allen F. Prusinowski, Henry C. Sise, Taylor N. Bednar, and David A. Nagib ACS Catal., 2022, 12, 4327−4332
Aza-heterocycles via copper-catalyzed, remote C–H desaturation of amines Leah M. Stateman †, Ross M. Dare †, Alyson N. Paneque, and David A. Nagib Chem, 2022, 8, 210–224 (open access)
Cross-Selective Aza-Pinacol Coupling via Atom Transfer Catalysis Sean M. Rafferty †, Joy E. Rutherford †, Lumin Zhang, Lu Wang, and David A. Nagib J. Am. Chem. Soc., 2021, 143, 5622–5628
Regioselective Radical Amino-Functionalizations of Allyl Alcohols via Dual Catalytic Cross-Coupling Zuxiao Zhang, Duong T. Ngo, and David A. Nagib ACS Catal., 2021, 11, 3473−3477
Enantioselective Radical C–H Amination for the Synthesis of β-Amino Alcohols Kohki M. Nakafuku †, Zuxiao Zhang †, Ethan A. Wappes †, Leah M. Stateman, Andrew D. Chen, and David A. Nagib Nature Chem., 2020, 12, 697–704 (open access)
Vicinal, Double C–H Functionalization of Alcohols via an Imidate Radical-Polar Crossover Cascade Allen F. Prusinowski, Raymond K. Twumasi, Ethan A. Wappes, and David A. Nagib J. Am. Chem. Soc., 2020, 142, 5429−5438
Radical Cascade Synthesis of Azoles via Tandem Hydrogen Atom Transfer Andrew D. Chen †, James H. Herbort †, Ethan A. Wappes, Kohki M. Nakafuku, Darsheed N. Mustafa, and David A. Nagib Chem. Sci., 2020, 11, 2479−2486
Chiral Piperidines from Acyclic Amines via Enantioselective, Radical-Mediated δ C–H Cyanation Zuxiao Zhang, Xin Zhang, and David A. Nagib Chem, 2019, 5, 3127−3134 (Open Access Pre-Print)
Development of an Imine Chaperone for Selective C–H Functionalization of Alcohols via Radical Relay Kohki M. Nakafuku †, Raymond K. Twumasi †, Avassaya Vanitcha †, Ethan A. Wappes, Kayambu Namitharan, Mathieu Bekkaye, and David A. Nagib J. Org. Chem., 2019, 84, 13065−13072
Multi-component Heteroarene Couplings via Polarity-reversed Radical Cascades Jeremy M. Lear †, J. Quentin Buquoi †, Xin Gu, Kui Pan, Darsheed N. Mustafa, and David A. Nagib Chem. Commun., 2019, 55, 8820−8823
Heteroarene Phosphinylalkylation via a Catalytic, Polarity-Reversing Radical Cascade J. Quentin Buquoi †, Jeremy M. Lear †, Xin Gu, and David A. Nagib ACS Catal., 2019, 9, 5330−5335
Catalytic β C–H amination via an imidate radical relay Leah M. Stateman, Ethan A. Wappes, Kohki M. Nakafuku, Kara M. Edwards, and David A. Nagib Chem. Sci., 2019, 10, 2693−2699
Site-Selective C–H Functionalization of (Hetero)Arenes via Transient, Non-symmetric Iodanes Stacy C. Fosu †, Chido M. Hambira †, Andrew D. Chen, James R. Fuchs, and David A. Nagib Chem, 2019, 5, 417−428 (Open Access)
δ C−H (Hetero)Arylation via Cu-Catalyzed Radical Relay Zuxiao Zhang, Leah M. Stateman, and David A. Nagib Chem. Sci., 2019, 10, 1207−1211
Ketyl radical reactivity via atom transfer catalysis Lu Wang, Jeremy M. Lear, Sean M. Rafferty, Stacy C. Fosu and David A. Nagib Science, 2018, 362, 225−229 (open access)
Catalytic Alkene Difunctionalization via Imidate Radicals Kohki M. Nakafuku †, Stacy C. Fosu †, and David A. Nagib J. Am. Chem. Soc., 2018, 140, 11202−11205
β C–H di-halogenation via iterative hydrogen atom transfer Ethan A. Wappes †, Avassaya Vanitcha †, and David A. Nagib Chem. Sci., 2018, 9, 4500–4504
Directed β C–H Amination of Alcohols via Radical Relay Chaperones Ethan A. Wappes †, Kohki M. Nakafuku †, and David A. Nagib J. Am. Chem. Soc., 2017, 139, 10204–10207
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