John F. Hartwig

University of California, Berkeley

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James P. Stambuli

AbbVie (United States)

C.D. Incarvito

Institut Charles Gerhardt Montpellier

Matthias Drieß

Technische Universität Berlin

Qilong Shen

Shanghai Institute of Organic Chemistry

Christopher D. Incarvito

Yale University

Douglas S. Clark

University of California, Berkeley

Shaozhong Ge

National University of Singapore

Grace Mann

Puma Biotechnology (United States)

Adam M. Johns

Materia (United States)

Jianrong Steve Zhou

Peking University

Cooperative Institutions

University of California, Berkeley

218

Yale University

121

Lawrence Berkeley National Laboratory

University of Illinois Urbana-Champaign

Chinese Academy of Sciences

Urbana University

Harvard University

Massachusetts Institute of Technology

California Institute of Technology

Centre National de la Recherche Scientifique

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Iridium-Catalyzed Arene Ortho-Silylation by Formal Hydroxyl-Directed C−H Activation

Journal of the American Chemical Society (2010)

Eric M. Simmons John F. Hartwig

A strategy for the ortho-silylation of aryl ketone, benzaldehyde, and benzyl alcohol derivatives has been developed in which a hydroxyl group formally serves as the directing element for Ir-catalyzed arene C−H bond activation. One-pot generation of a (hydrido)silyl ether from the carbonyl compound or alcohol is followed by dehydrogenative cyclization at 80−100 °C in the presence of norbornene as a hydrogen acceptor and the combination of 1 mol % [Ir(cod)OMe]2 and 1,10-phenanthroline as a catalyst to form benzoxasiloles. The synthetic utility of the benzoxasilole products is demonstrated by conversion to phenol or biaryl derivatives by Tamao−Fleming oxidation or Hiyama cross-coupling. Both of these transformations of the C−H silylation products exploit the Si−O bond in the system and proceed by activation of the silyl moiety with hydroxide, rather than fluoride.

Moiety

Silyl ether

Benzaldehyde

10.1021/ja1086547

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Citations (235)

Palladium-Catalyzed Amination of Aromatic C−H Bonds with Oxime Esters

Journal of the American Chemical Society (2010)

Yichen Tan John F. Hartwig

We report a conceptually new approach to the direct amination of aromatic C−H bonds. In this process, an oxime ester function reacts with an aromatic C−H bond under redox-neutral conditions to form, in the case studied, an indole product. These reactions occur with relatively low catalyst loading (1 mol %) by a mechanism that appears to involve an unusual initial oxidative addition of an N−O bond to a Pd(0) species. The Pd(II) complex from oxidative addition of the N−X bond has been isolated for the first time, and evidence for the intermediacy of such oxidative addition products in the catalytic reaction has been gained.

10.1021/ja100676r

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Citations (536)

Iridium‐Catalyzed Regio‐ and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles

Angewandte Chemie (2016)

Ming Chen John F. Hartwig

Abstract The first Ir‐catalyzed enantioselective allylation of trisubstituted allylic electrophiles has been developed. Through modification of the leaving group of allylic electrophiles, we found that trisubstituted allylic phosphates are suitable electrophiles for asymmetric allylation. The reaction of allylic phosphates with enol silanes derived from dioxinones gave allylated products in good yields with high enantioselectivities.

Substitution reaction

Silanes

10.1002/ange.201607053

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Citations (11)

Iridium‐Catalyzed Regio‐ and Enantioselective N‐Allylation of Indoles

Angewandte Chemie International Edition (2009)

Levi M. Stanley John F. Hartwig

Iridium is blind to C: Highly regio- and enantioselective, iridium-catalyzed N-allylations of indoles, which complement the more common reactivity of indoles as carbon nucleophiles, have been developed (see scheme). These reactions form highly enantioenriched N-allylindoles, which are readily transformed into enantioenriched 3-(1H-indol-1-yl)-N-methyl-3-aryl propan-1-amines, dihydropyrrolo[1,2-a]indoles, and indol-1-yl propanoic acids.

Reactivity

10.1002/anie.200904338

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Citations (168)

Catalyzed carbon-heteroatom bond formation

Wiley-VCH eBooks (2011)

Andrei K. Yudin John F. Hartwig

Synthesis of Saturated Five-Membered Nitrogen Heterocycles via Pd-Catalyzed C-N Bond-Forming Reactions Transition Metal Catalyzed Approaches to Lactones Involving C-O Bond Formation The Formation of Csp2-S and Csp2-Se Bonds by Substitution and Addition Reactions Catalyzed by Transition Metal Complexes Palladium-Catalysis for Oxidative 1,2-Difunctionalization of Alkenes Rhodium-Catalyzed C-H Aminations The Palladium Catalyzed Synthesis of Aromatic Heterocycles New Reactions of Copper Acetylides: Catalytic Dipolar Cycloadditions and Beyond Transition Metal-Catalyzed Synthesis of Monocyclic Five-Membered Aromatic Heterocycles Transition Metal-Catalyzed Synthesis of Fused Five-Membered Aromatic Heterocycles Carbon-Heteroatom Bond Formation by RhI-Catalyzed Ring-Opening Reactions Gold-Catalyzed Addition of Nitrogen and Sulfur Nucleophiles to C-C Multiple Bonds Gold-Catalyzed Addition of Oxygen Nucleophiles to C-C Multiple Bonds

Heteroatom

Oxidative addition

Source

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Citations (42)

Forcieren der σ‐Donorstärke in Iridium‐Pinzettenkomplexen: Bis(silylen)‐ und Bis(germylen)‐Liganden sind stärkere Donoren als Bis[phosphor(III)]‐Liganden

Angewandte Chemie (2012)

Andreas Brück Daniel Gallego Wenyuan Wang Elisabeth Irran Matthias Drieß

Auf der Suche nach dem Limit: Die einzigartige Koordinationschemie von ECHE-Liganden (E=Si, Ge) mit Übergangsmetallen der 9. Gruppe (Ir, Rh) sowie die Anwendung der Komplexe in der katalytischen C-H-Borylierung von Arenen wurden untersucht. Ein Vergleich von Iridiumkomplexen zeigt, dass die divalenten Si- und Ge-Pinzettenliganden in ihren σ-Donoreigenschaften den isoelektronischen PIII-Ligandsystemen überlegen sind.

10.1002/ange.201205570

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Citations (50)

CCDC 1026506: Experimental Crystal Structure Determination

The Cambridge Structural Database (2014)

Joseph S. Bair York Schramm Alexey G. Sergeev Eric Clot Odile Eisenstein

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/cc13g53v

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Citations (0)

Regioselective, Asymmetric Formal Hydroamination of Unactivated Internal Alkenes

Angewandte Chemie International Edition (2015)

Yumeng Xi Trevor W. Butcher Jing Zhang John F. Hartwig

Abstract We report the regioselective and enantioselective formal hydroamination of unsymmetrical internal alkenes catalyzed by a copper catalyst ligated by DTBM‐SEGPHOS. The regioselectivity of the reaction is controlled by the electronic effects of ether, ester, and sulfonamide groups in the homoallylic position. The observed selectivity underscores the influence of inductive effects of remote substituents on the selectivity of catalytic processes occurring at hydrocarbyl groups, and the method provides direct access to various 1,3‐aminoalcohol derivatives with high enantioselectivity.

Hydroamination

Sulfonamide

10.1002/anie.201509235

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Citations (132)

CCDC 1980832: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Bo Su Ala Bunescu Yehao Qiu Stephan J. Zuend Martin Ernst

10.5517/ccdc.csd.cc24h6tp

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Citations (0)

CCDC 795915: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

Zheng Huang Jianrong Zhou John F. Hartwig

10.5517/ccvq6pf

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Citations (0)