Takacs, James - University of Nebraska-Lincoln

个人简介

Dr. Takacs received his bachelor's degree from Rutgers University (1976) where he carried out undergraduate research under the direction of Dr. Paul Hudrlik and his doctorate from Caltech (1981) where he studied under Dr. David A. Evans. After postdoctoral studies under Dr. Albert Eschenmoser at ETH-Zurich (1981-82), he was appointed Assistant Professor of Chemistry at the University of Utah (1982). He moved to the University of Nebraska-Lincoln in 1988 where he is currently Charles J. Mach University Professor in Chemistry (2011-pres). Dr. Takacs received the UNL College of Arts and Science Outstanding Research and Creative Achievement Award in the Sciences (2008) and served as Chemistry Department Chair (2007-2013). Along with numerous undergraduate coworkers, more than 60 graduate students and postdocs have trained in the Takacs labs. Postdoctoral, Swiss National Funds International Postdoctoral Fellow, Swiss Federal Institute of Technology Ph.D., California Institute of Technology B.S., Rutgers University

研究领域

Asymmetric Catalysis, Self-Assembly, Combinatorial Catalysis, Metal-Catalyzed Cyclizations, Synthetic Methods Development, Natural Product Total Synthesis Current Research Catalytic Asymmetric Hydroboration (CAHB) has been around for a long time, and many outstanding research groups have contributed to understanding this (fiendishly complex) catalyzed counterpart of the classic stoichiometric reaction.[i] Now, as new methods rapidly evolve using chiral secondary and tertiary boronic esters for stereospecific carbon-carbon bond construction,[ii] the development of new catalyst systems and the exploration of new substrates for CAHB are enjoying renewed interest. Recent work in the Takacs group has focused on developing the CAHB, mostly rhodium-catalyzed CAHBs, of substrates capable of two-point binding to the metal center. The observation of unusual Markovnikov regioselectivity leading to chiral tertiary boronic esters is among the important advances. For example, we recently published a simple, in situ-generated, chiral rhodium catalyst for which methylidene and trisubstituted alkene substrates form chiral tertiary boronic esters (up to 87% yield and 96:4 enantiomer ratio (er)) via oxime-directed CAHB. Subsequent C–C coupling is used to form a quaternary all carbon stereocenter, while other transformations lead to chiral diols, O-substituted hydroxylamines, and isoxazolines.[iii] Similarly, as illustrated below, phosphonate-derived CAHB affords new, bifunctional chiral tertiary boronic ester synthons suitable for further elaboration.[iv] Recently, it has been discovered that H2 will “hitch a ride” on the CAHB catalyst interrupting hydroboration to arrive at efficient Catalytic Asymmetric Hydrogenation (CAH).[v]

近期论文

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Ligand-Controlled Regiodivergent Enantioselective Rhodium-Catalyzed Alkene Hydroboration. Andrew J. Bochat, Veronika M. Shoba and James M. Takacs. Angew. Chem., Int. Ed. Accepted Article. DOI: 10.1002/anie.201903308 Takacs Publication Bis(norbornadiene)rhodium(I) Tetrafluoroborate (Review). Suman Chakrabarty, Veronika M. Shoba and James M. Takacs. EROS Encyclopedia of Reagents for Organic Synthesis. 2019. Facile Access to Functionalized Chiral Secondary Benzylic Boronic Esters via Catalytic Asymmetric Hydroboration. Suman Chakrabarty, Hector Palencia, Martha D. Morton, Ryan O. Carr and James M. Takacs.Chem. Sci., 2019, 10, 4854-4861. This work was highlighted in UNL Chemistry webpage: Adding boron is anything but boring.... Suman Phosphonate-Directed Catalytic Asymmetric Hydroboration: Delivery of Boron to the More Substituted Carbon, Leading to Chiral Tertiary Benzylic Boronic Esters. Suman Chakrabarty and James M. Takacs. ACS Catal., 2018, 8, 10530-10536. Takacs Publication Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides. Gia L. Hoang, Shuyang Zhang and James M. Takacs. Chem. Commun., 2018, 54, 4838-4841. Graphical abstract: Rhodium-catalyzed asymmetric hydroboration of Î³,Î´-unsaturated amide derivatives: Î´-borylated amides Enantioselective γ‐Borylation of Unsaturated Amides and Stereoretentive Suzuki‐Miyaura Cross‐Coupling. Gia L. Hoang and James M. Takacs. Chem. Sci., 2017, 8, 4511-4516. Takacs PublicationThis paper is highlighted in Synfacts (Link) Synthesis of Chiral Tertiary Boronic Esters: Phosphonate-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes. Suman Chakrabarty and James M. Takacs. J. Am. Chem. Soc., 2017, 139, 6066-6069. Takacs Publication Remarkably Facile Borane-Promoted, Rhodium-Catalyzed Asymmetric Hydrogenation of Tri- and Tetrasubstituted Alkenes. Veronika M. Shoba and James M. Takacs. J. Am. Chem. Soc., 2017, 139 (16), 5740–5743.Takacs PublicationThis paper is highlighted in Synfacts (Link). Click here to view an ACS presentation on demand on Oxime-directed catalytic asymmetric hydrogenation (CAH): Tri- and Tetrasubstituted alkenes presented by Dr. James M. Takacs. Ruthenium-Catalyzed Amination of Secondary Alcohols Using Borrowing Hydrogen Methodology. Kostiantyn O. Marichev and James M. Takacs. ACS Catal., 2016, 6, 2205–2210.Takacs Publication Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration. Veronika M. Shoba, Nathan C. Thacker, Andrew J. Bochat and James M. Takacs. Angew. Chem. Int. Ed. 2016, 55, 1465-1469.Takacs Publication Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki-Miyaura Cross-Coupling. Gia L. Hoang, Zhao-Di Yang, Sean M. Smith, Rhitankar Pal, Judy L. Miska, Damaris E. Pérez, Libbie S. W. Pelter, Xiao Cheng Zeng, and James M. Takacs. Org. Lett., 2015, 17 (4), 940–943.Takacs Publication Surprisingly facile C-H activation in the course of oxime-directed catalytic asymmetric hydroboration. Nathan C. Thacker, Veronika M. Shoba, Andrew E. Geis and James M. Takacs. Tetrahedron Letters 2015, 56 (23), 3306-3310. Mechanistic Insights into Carbonyl-Directed Rhodium-Catalyzed Hydroboration: ab Initio Study of a Cyclic γ,δ-Unsaturated Amide. Zhao-Di Yang, Rhitankar Pal, Gia L. Hoang, Xiao Cheng Xeng and James M Takacs. ACS Catal., 2014, 4 (3), 763–773.Takacs Publication Preparation of D-cycloserine and 13C-labeled D-cycloserine. Nathan C. Thacker, Judit Molnar-Toth, Judy L. Miska, Raul G Barletta and James M. Takacs. Heterocycles 2012, 86, 1575-1582. Ligand Scaffold Optimization of a Supramolecular Hydrogenation Catalyst: Analyzing the Influence of Key Structural Subunits on Reactivity and Selectivity. Nathan C. Thacker, Shin A. Moteki, James M. Takacs. ACS Catal., 2012, 2, 2743-2752. γ-Selective Directed Catalytic Asymmetric Hydroboration of 1,1-Disubstituted Alkenes. Sean M Smith , Gia L. Hoang , Rhitankar Pal , Mohammad O. Bani Khaled , Liberty S. W. Pelter , Xiao Cheng Zeng and James M. Takacs. Chem. Commun., 2012, 48, 12180-12182. Takacs Publication Two-Stage Optimization of a Supramolecular Catalyst for Catalytic Asymmetric Hydroboration. Shin A. Moteki, Kazuya Toyama, Zeyu Liu, Jing Ma, Andrea Holmes and James M. Takacs. Chem. Commun., 2012,48, 263-265. Catalytic Asymmetric Hydroboration of β,γ-Unsaturated Weinreb Amides: Surprising Influence of the Borane. Sean M. Smith and James M. Takacs. Chem. Commun., 2011, 47, 7812-7814. Remarkable Levels of Enantioswitching in Catalytic Asymmetric Hydroboration. Sean M. Smith and James M. Takacs. Org. Lett., 2010, 12, 4612–4615. Vibrational properties of ferroelectric β-vinylidene fluoride polymers and oligomers. Serge M. Nakhmanson, R. Korlacki, J. Travis Johnston, Stephen Ducharme, Zhongxin Ge and James M. Takacs. Phys. Rev. B, 2010, 81, 174120.