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Daniel J. Weix

University of Wisconsin–Madison

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William W. Brennessel

University of Rochester

Daniel A. Everson

University of Rochester

Ruja Shrestha

University of Rochester

Laura K. G. Ackerman

Emory University

Patrick L. Holland

Yale University

Michael M. Gilbert

University of Wisconsin–Madison

Ilia A. Guzei

University of Wisconsin–Madison

Shannon S. Stahl

University of Wisconsin–Madison

Jiang Wang

University of Wisconsin–Madison

Chi Chen

Hubei University

Cooperative Institutions

University of Wisconsin–Madison

University of Rochester

Yale University

Pfizer (United States)

University of Illinois Urbana-Champaign

Emory University

Merck & Co., Inc., Rahway, NJ, USA (United States)

University of California, Berkeley

University of Michigan–Ann Arbor

California Institute of Technology

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Asymmetric Synthesis of Protected Arylglycines by Rhodium‐Catalyzed Addition of Arylboronic Acids to N‐tert‐Butanesulfinyl Imino Esters.

ChemInform (2006)

Melissa A. Beenen Daniel J. Weix Jonathan A. Ellman

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

10.1002/chin.200639208

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Citations (4)

Ketones from Nickel‐Catalyzed Decarboxylative, Non‐Symmetric Cross‐Electrophile Coupling of Carboxylic Acid Esters

Angewandte Chemie International Edition (2019)

Jiang Wang Brian P. Cary Peyton D. Beyer Samuel H. Gellman Daniel J. Weix

Abstract Synthesis of the C−C bonds of ketones relies upon one high‐availability reagent (carboxylic acids) and one low‐availability reagent (organometallic reagents or alkyl iodides). We demonstrate here a ketone synthesis that couples two different carboxylic acid esters, N ‐hydroxyphthalimide esters and S ‐2‐pyridyl thioesters, to form aryl alkyl and dialkyl ketones in high yields. The keys to this approach are the use of a nickel catalyst with an electron‐poor bipyridine or terpyridine ligand, a THF/DMA mixed solvent system, and ZnCl 2 to enhance the reactivity of the NHP ester. The resulting reaction can be used to form ketones that have previously been difficult to access, such as hindered tertiary/tertiary ketones with strained rings and ketones with α‐heteroatoms. The conditions can be employed in the coupling of complex fragments, including a 20‐mer peptide fragment analog of Exendin(9–39) on solid support.

Decarboxylation

10.1002/anie.201906000

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Citations (116)

Discussion Addendum for: Nickel‐Catalyzed Cross‐Coupling of Aryl Halides with Alkyl Halides: Ethyl 4‐(4‐(4‐Methylphenylsulfonamido)‐Phenyl)butanoate

Organic Syntheses (2023)

Daniel C. Salgueiro Lauren E. Ehehalt Keywan A. Johnson Daniel J. Weix

Abstract This chapter describes the procedure for nickel‐catalyzed cross‐coupling of aryl halides with alkyl halides: ethyl 4‐(4‐(4‐methylphenylsulfonamido)‐phenyl)butanoate. It presents some of the important points to be considered, the conditions that need to be maintained, characterization data, and the reagents required, as well as the techniques used and the equipment setup that are vital to carrying out the process. The chapter also describes the hazards associated with working with chemicals and the ways to deal with these hazards. While alkyl halides are far more abundant than alkyl organometallic reagents, the largest commercially available pools of aliphatic electrophile diversity are alcohols, amines, and alkanoic acids.

10.1002/0471264229.os099.15

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Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers

Organic Letters (2017)

Kierra M. M. Huihui Ruja Shrestha Daniel J. Weix

Conjugate addition of organometallic reagents to enones to form silyl enol ether products is a versatile method to difunctionalize activated olefins, but the organometallic reagents required can be limiting. The reductive cross-electrophile coupling of unhindered primary alkyl bromides with enones and chlorosilanes to form silyl enol ether products is catalyzed by a nickel-complexed ortho-brominated terpyridine ligand. The conditions are compatible with a variety of cyclic/acyclic enones and functional groups.

Conjugate

Primary (astronomy)

Reductive elimination

Addition reaction

10.1021/acs.orglett.6b03509

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Citations (27)

The hydrogen-bonding dynamics of water to a nitrile-functionalized electrode is modulated by voltage according to ultrafast 2D IR spectroscopy

Proceedings of the National Academy of Sciences (2023)

Matthew J. Ryan Nan Yang Kijeong Kwac Kiera B. Wilhelm K. Benjamin

We report the hydrogen-bonding dynamics of water to a nitrile-functionalized and plasmonic electrode surface as a function of applied voltage. The surface-enhanced two-dimensional infrared spectra exhibit hydrogen-bonded and non-hydrogen-bonded nitrile features in similar proportions, plus cross peaks between the two. Isotopic dilution experiments show that the cross peaks arise predominantly from chemical exchange between hydrogen-bonded and non-hydrogen-bonded nitriles. The chemical exchange rate depends upon voltage, with the hydrogen bond of the water to the nitriles breaking 2 to 3 times slower (>63 vs. 25 ps) under a positive as compared to a negative potential. Spectral diffusion created by hydrogen-bond fluctuations occurs on a ~1 ps timescale and is moderately potential-dependent. Timescales from molecular dynamics simulations agree qualitatively with the experiment and show that a negative voltage causes a small net displacement of water away from the surface. These results show that the voltage applied to an electrode can alter the timescales of solvent motion at its interface, which has implications for electrochemically driven reactions.

10.1073/pnas.2314998120

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Citations (8)

Reductive Arylation of Nitroarenes with Chloroarenes: Reducing Conditions Enable New Reactivity from Palladium Catalysts

Brett Akana-Schneider Daniel J. Weix

Palladium-catalyzed C–N bond forming reactions are a key tool in modern synthetic organic chemistry. Despite advances in catalyst design enabling the use of a variety of aryl (pseudo)halides, the neces-sary aniline coupling partner is often synthesized in a discrete reduc-tion step from a nitroarene. An ideal synthetic sequence would avoid the necessity of this step while maintaining the reliable reactivity of palladium catalysis. Herein we describe how reducing conditions enable new chemical steps and reactivity from well-studied palladium catalysts, resulting in a new, useful transformation: the reductive arylation of nitroarenes with chloroarenes to form diarylamines. Mechanistic experiments suggest that under reducing conditions, BrettPhos-palladium complexes catalyze the dual N-arylation of typi-cally inert azoarenes—generated via the in situ reduction of ni-troarenes—via two distinct mechanisms. Initial N-arylation proceeds via a novel association-reductive palladation sequence followed by reductive elimination to yield an intermediate 1,1,2-triarylhydrazine. Arylation of this intermediate by the same catalyst via a traditional amine arylation sequence forms a transient tetraarylhydrazine, un-locking reductive N–N bond cleavage to liberate the desired product. The resulting reaction allows for the synthesis of diarylamines bearing a variety of synthetically valuable functionalities and heteroaryl cores in high yield.

Reductive elimination

Reactivity

Aryl halide

Organic Synthesis

10.26434/chemrxiv-2023-vh0td-v2

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Citations (1)

Regio- and Enantioselective Iridium-Catalyzed Allylation of Enamines

Synfacts (2007)

Daniel J. Weix John F. Hartwig

This is a nice report for the indirect allylation of ketones. The authors expertly use enamine chemistry to access high regio- and enantioselectivity. Use of a iridium(cod)-phosphoramidite complex gave the branched product with high selectivity. Interestingly, ZnCl2 was added to trap the liberated isopropanol.

Phosphoramidite

Enamine

10.1055/s-2007-968865

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Decarboxylative Cross-Coupling Enabled by Fe and Ni Metallaphotoredox Catalysis

Reem Nsouli Sneha Nayak Venkadesh Balakrishnan Jung-Ying Lin K. Benjamin

Decarboxylative cross-coupling of carboxylic acids and aryl halides has become a key transformation in organic synthe- sis to form C(sp2)–C(sp3) bonds. In this report, a base metal pairing between Fe and Ni has been developed with complementary reactivity to the well-established Ir and Ni metallaphotoredox reactions. Utilizing an inexpensive FeCl3 co-catalyst along with a pyr- idine carboxamidine Ni catalyst, a range of aryl iodides can be preferentially coupled to carboxylic acids over boronic acid esters, triflates, chlorides, and even bromides in high yields. Additionally, carboxylic acid derivatives containing heterocycles, N-protected amino acids, electron-rich amines, and protic functionality can be coupled in 23-96% yield with a range of sterically hindered, elec- tron-rich, and electron-deficient aryl iodides. Preliminary catalytic and stoichiometric reactions support a mechanism in which Fe is responsible for the activation of carboxylic acid upon irradiation with light and a Ni(I)alkyl intermediate is responsible for activation of the aryl iodide coupling partner followed by reductive elimination to generate product.

Reactivity

Reductive elimination

Coupling reaction

10.26434/chemrxiv-2024-dmfhw

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Citations (1)

Synthesis of Functionalized Dialkyl Ketones from Carboxylic Acid Derivatives and Alkyl Halides

Organic Letters (2012)

Alexander C. Wotal Daniel J. Weix

Unsymmetrical dialkyl ketones can be directly prepared by the nickel-catalyzed reductive coupling of carboxylic acid chlorides or (2-pyridyl)thioesters with alkyl iodides or benzylic chlorides. A wide variety of functional groups are tolerated by this process, including common nitrogen protecting groups and C–B bonds. Even hindered ketones flanked by tertiary and secondary centers can be formed. The mechanism is proposed to involve the reaction of a (L)Ni(alkyl)2 intermediate with the carboxylic acid derivative.

10.1021/ol300217x

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Citations (158)

Control of Redox‐Active Ester Reactivity Enables a General Cross‐Electrophile Approach to Access Arylated Strained Rings**

Angewandte Chemie (2022)

Daniel C. Salgueiro K. Benjamin Ilia A. Guzei Pablo García‐Reynaga Daniel J. Weix

Abstract Strained rings are increasingly important for the design of pharmaceutical candidates, but cross‐coupling of strained rings remains challenging. An attractive, but underdeveloped, approach to diverse functionalized carbocyclic and heterocyclic frameworks containing all‐carbon quaternary centers is the coupling of abundant strained‐ring carboxylic acids with abundant aryl halides. Herein we disclose the development of a nickel‐catalyzed cross‐electrophile approach that couples a variety of strained ring N ‐hydroxyphthalimide (NHP) esters, derived from the carboxylic acid in one step, with various aryl and heteroaryl halides under reductive conditions. The chemistry is enabled by the discovery of methods to control NHP ester reactivity, by tuning the solvent or using modified NHP esters, and the discovery that t‐ Bu BpyCam CN , an L2X ligand, avoids problematic side reactions. This method can be run in flow and in 96‐well plates.

Reactivity

Coupling reaction

10.1002/ange.202205673

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Citations (7)

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