Tomislav Rovis
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View article: Regioisomeric Tuning of Intermolecular Diels‐Alder Reaction by Electrostatic Field‐Dipole Interaction
Regioisomeric Tuning of Intermolecular Diels‐Alder Reaction by Electrostatic Field‐Dipole Interaction Open
The effect of an electric field on the regioselectivity of the Diels‐Alder reaction is explored using a zwitterionic iminium ion species as both the dienophile and the source of the electric field. The head‐to‐tail dipolar orientation of t…
View article: Rh(III)-Catalyzed Alkene <i>Anti</i> Nucleoamidation to Access Diverse Heterocycles
Rh(III)-Catalyzed Alkene <i>Anti</i> Nucleoamidation to Access Diverse Heterocycles Open
Alkene difunctionalization methods are an attractive way to rapidly build molecular complexity using readily available starting materials. One common approach is transition metal-catalyzed nucleometalation, which converts the C-C double bo…
View article: Photoredox‐Catalyzed Generation of Tertiary Anions from Primary Amines via a Radical Polar Crossover
Photoredox‐Catalyzed Generation of Tertiary Anions from Primary Amines via a Radical Polar Crossover Open
A method for the generation of tertiary carbanions via a deaminative radical‐polar crossover is reported using redox active imines from α‐tertiary primary amines. A variety of benzylic amines and amino esters can be used in this approach, …
View article: Rhodium(III)-Catalyzed Remote Hydroamidation of Internal Alkenes Via Chain Walking
Rhodium(III)-Catalyzed Remote Hydroamidation of Internal Alkenes Via Chain Walking Open
Hydroamination of terminal alkenes represents a powerful and well-established way to introduce nitrogenous functionality to feedstock chemicals. Remote hydroamination reactions are far less known, and represent a way to functionalize unact…
View article: Late-Stage Isotopic Exchange of Primary Amines
Late-Stage Isotopic Exchange of Primary Amines Open
Stable isotopes such as 2H, 13C, and 15N have important applications in chemistry and drug discovery. Late-stage incorporation of uncommon isotopes via isotopic exchange allows for the direct conversion of complex molecules into their valu…
View article: Photocatalytic Activation of Aryl(trifluoromethyl) Diazos to Car-benes for High-Resolution Protein Labeling with Red Light
Photocatalytic Activation of Aryl(trifluoromethyl) Diazos to Car-benes for High-Resolution Protein Labeling with Red Light Open
State-of-the-art methods in photo-proximity labeling center on the targeted generation and capture of short-lived re-active intermediates to provide a snapshot of local protein environments. Diazirines are the current gold standard for hig…
View article: Photoinduced Nickel-Catalyzed Selective <i>N</i>-Demethylation of Trialkylamines Using C(sp<sup>2</sup>)–Bromides as HAT Reagents
Photoinduced Nickel-Catalyzed Selective <i>N</i>-Demethylation of Trialkylamines Using C(sp<sup>2</sup>)–Bromides as HAT Reagents Open
N-Demethylation of trialkylamines is a useful transformation, but typically requires harsh reaction conditions and stepwise procedures, as well as judicious protection of labile functional groups. Herein we report a mild, catalytic approac…
View article: Red-Shifting Blue Light Photoredox Catalysis for Organic Synthesis: A Graphical Review
Red-Shifting Blue Light Photoredox Catalysis for Organic Synthesis: A Graphical Review Open
Photoredox catalysis has revolutionized synthetic chemistry in recent decades. However, the field has traditionally used high-energy blue/ultraviolet light to activate chromophores. High-energy irradiation is associated with several drawba…
View article: Coupling of α-bromoamides and unactivated alkenes to form γ-lactams through EDA and photocatalysis
Coupling of α-bromoamides and unactivated alkenes to form γ-lactams through EDA and photocatalysis Open
γ-Lactams are privileged heterocycles on route to the synthesis of pharmaceuticals. Herein, we demonstrate the facile synthesis of variously substituted γ-lactams utilizing electron donor–acceptor (EDA) complexes of amines and α-Br-amides.
View article: Modular Synthesis of Unnatural Peptides via Rh(III)-Catalyzed Diastereoselective Three-Component Carboamidation Reaction
Modular Synthesis of Unnatural Peptides via Rh(III)-Catalyzed Diastereoselective Three-Component Carboamidation Reaction Open
Herein we report a modular peptide ligation methodology that couples dioxazolones, arylboronic acids, and acrylamides to construct amide bonds in a diastereoselective manner under mild conditions, facilitated by Rh(III) catalysis. By conve…
View article: Rhodium(III)-Catalyzed Anti-Markovnikov Hydroamidation of Unactivated Alkenes Using Dioxazolones as Amidating Reagents
Rhodium(III)-Catalyzed Anti-Markovnikov Hydroamidation of Unactivated Alkenes Using Dioxazolones as Amidating Reagents Open
The amide is one of the most prevalent functional groups in all of pharmaceuticals, and for this reason, reactions that introduce the amide moiety are of particular value. Intermolecular hydroamidation of alkenes remains an underexplored m…
View article: Rh(III)-Catalyzed Intra- and Intermolecular 3,4-Difunctionalization of 1,3-Dienes via Rh(III)-π-Allyl Amidation with 1,4,2-Dioxazolones
Rh(III)-Catalyzed Intra- and Intermolecular 3,4-Difunctionalization of 1,3-Dienes via Rh(III)-π-Allyl Amidation with 1,4,2-Dioxazolones Open
We herein report a modular strategy, which enables Rh(III)-catalyzed diastereoselective 3,4-amino oxygenation and diamination of 1,3-dienes using different O- and N-nucleophiles in combination with readily available 3-substituted 1,4,2-dio…
View article: CCDC 2179311: Experimental Crystal Structure Determination
CCDC 2179311: Experimental Crystal Structure Determination Open
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 …
View article: Tuning through-space interactions <i>via</i> the secondary coordination sphere of an artificial metalloenzyme leads to enhanced Rh(<scp>iii</scp>)-catalysis
Tuning through-space interactions <i>via</i> the secondary coordination sphere of an artificial metalloenzyme leads to enhanced Rh(<span>iii</span>)-catalysis Open
We report computationally-guided protein engineering of monomeric streptavidin Rh( iii ) artificial metalloenzyme to enhance catalysis of the enantioselective coupling of acrylamide hydroxamate esters and styrenes.
View article: Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products
Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products Open
Oximes are valuable synthetic intermediates for the preparation of a variety of functional groups. To date, the stereoselective synthesis of oximes remains a major challenge, as most current synthetic methods either provide mixtures of E a…
View article: Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines
Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines Open
We report a method to activate α-3° amines for deaminative arylation via condensation with an electron-rich aldehyde and merge this reactivity with nickel metallaphotoredox to generate benzylic quaternary centers, a common motif in pharmac…
View article: Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis
Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis Open
Redox processes are at the heart of synthetic methods that rely on either electrochemistry or photoredox catalysis, but how do electrochemistry and photoredox catalysis compare? Both approaches provide access to high energy intermediates (…
View article: Site-Selective α-C–H Functionalization of Trialkylamines via Reversible Hydrogen Atom Transfer Catalysis
Site-Selective α-C–H Functionalization of Trialkylamines via Reversible Hydrogen Atom Transfer Catalysis Open
Trialkylamines are widely found in naturally occurring alkaloids, synthetic agrochemicals, biological probes, and especially pharmaceuticals agents and preclinical candidates. Despite the recent breakthrough of catalytic alkylation of dial…
View article: Tuning the Electrochemical and Photophysical Properties of Osmium Complexes for Application in Photoredox Catalysis
Tuning the Electrochemical and Photophysical Properties of Osmium Complexes for Application in Photoredox Catalysis Open
Photocatalysis driven by visible and ultraviolet irradiation is a fundamental tool for synthetic chemists. Recently, expansion of this tool to near-infrared (NIR) light has gained in popularity. Herein, we report the detailed photophysical…
View article: Tuning the Electrochemical and Photophysical Properties of Osmium Complexes for Application in Photoredox Catalysis
Tuning the Electrochemical and Photophysical Properties of Osmium Complexes for Application in Photoredox Catalysis Open
Photocatalysis driven by visible and ultraviolet irradiation is a fundamental tool for synthetic chemists. Recently, expansion of this tool to near-infrared (NIR) light has gained in popularity. Herein, we report the detailed photophysical…
View article: Diastereoselective Three-Component 3,4-Amino Oxygenation of 1,3-Dienes Catalyzed by a Cationic Heptamethylindenyl Rhodium(III) Complex
Diastereoselective Three-Component 3,4-Amino Oxygenation of 1,3-Dienes Catalyzed by a Cationic Heptamethylindenyl Rhodium(III) Complex Open
The direct oxyamination of olefins is a compelling tool to rapidly access β-amino alcohols-a privileged motif ubiquitous in natural products, pharmaceuticals and agrochemicals. Although a variety of expedient methods are established for si…
View article: Targeted Activation in Localized Protein Environments via Deep Red Photoredox Catalysis
Targeted Activation in Localized Protein Environments via Deep Red Photoredox Catalysis Open
State-of-the art photoactivation strategies in chemical biology provide spatiotemporal control and visualization of biological processes. However, using high energy light (λ < 500 nm) for substrate or photocatalyst sensitization can lead t…
View article: Targeted Activation in Localized Protein Environments via Deep Red Photoredox Catalysis
Targeted Activation in Localized Protein Environments via Deep Red Photoredox Catalysis Open
State-of-the art photoactivation strategies in chemical biology provide spatiotemporal control and visualization of biological processes. However, using high energy light (λ < 500 nm) for substrate or photocatalyst sensitization can lead t…
View article: Late-Stage <i>N</i>-Me Selective Arylation of Trialkylamines Enabled by Ni/Photoredox Dual Catalysis
Late-Stage <i>N</i>-Me Selective Arylation of Trialkylamines Enabled by Ni/Photoredox Dual Catalysis Open
The diversity and wide availability of trialkylamines render them ideal sources for rapid construction of complex amine architectures. Herein, we report that a nickel/photoredox dual catalysis strategy affects site-selective α-arylation of…
View article: CCDC 2062316: Experimental Crystal Structure Determination
CCDC 2062316: Experimental Crystal Structure Determination Open
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 …