Michael C. Willis
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View article: Site-Selective C–H Sulfinamidation through Electron-Donor–Acceptor Complex Photoactivation and Radical Addition into Sulfinylamine Reagents
Site-Selective C–H Sulfinamidation through Electron-Donor–Acceptor Complex Photoactivation and Radical Addition into Sulfinylamine Reagents Open
Aryl sulfinamides are versatile synthetic intermediates for accessing diverse and medicinally relevant S(VI) functionalities, such as sulfonamides and sulfonimidamides. Herein, we report a thianthrenium-enabled, site-selective C-H sulfinam…
View article: A modular synthesis of azetidines from reactive triplet imine intermediates using an intermolecular aza Paternò–Büchi reaction
A modular synthesis of azetidines from reactive triplet imine intermediates using an intermolecular aza Paternò–Büchi reaction Open
View article: Iron-Catalyzed Decarboxylative Sulfinylation of Alkyl Carboxylic Acids
Iron-Catalyzed Decarboxylative Sulfinylation of Alkyl Carboxylic Acids Open
Sulfinamides, sulfonamides, and sulfonimidamides are valuable motifs in medicinal chemistry, yet methods to synthesize alkyl variants from simple, readily available feedstocks remain scarce. In this report, we detail the synthesis of these…
View article: Desulfinative Cross-Coupling as a Method to Overcome Problematic Suzuki–Miyaura Reactions of Pharmaceutically Relevant Heteroaromatic Boronates
Desulfinative Cross-Coupling as a Method to Overcome Problematic Suzuki–Miyaura Reactions of Pharmaceutically Relevant Heteroaromatic Boronates Open
The well documented difficulties associated with direct (hetero)-arylation of aza-aromatics (e.g., azines) at the α-position to nitrogen led to a collaborative project between the Willis group at Oxford and the Medicine Design depar…
View article: Asymmetric reductive arylation and alkenylation to access S-chirogenic sulfinamides
Asymmetric reductive arylation and alkenylation to access S-chirogenic sulfinamides Open
The study of the stereochemistry of organic sulfur compounds has been ongoing for over a century, with S-chirogenic pharmacophores playing an essential role in drug discovery within bioscience and medicinal chemistry. Traditionally, the sy…
View article: Synthesis and functionalization of vinyl sulfonimidamides and their potential as electrophilic warheads
Synthesis and functionalization of vinyl sulfonimidamides and their potential as electrophilic warheads Open
Vinyl sulfonimidamides are effective electrophilic groups for reaction with both sulfur- and nitrogen-based biologically relevant nucleophiles. We show that the reactivity of these new reagents can be modulated by choice of the imidic N -s…
View article: Friedel–Crafts Reactivity with Sulfondiimidoyl Fluorides for the Synthesis of Heteroaryl Sulfondiimines
Friedel–Crafts Reactivity with Sulfondiimidoyl Fluorides for the Synthesis of Heteroaryl Sulfondiimines Open
Sulfur functional groups are ubiquitous in molecules used in the pharmaceutical and agrochemical industries, and within these collections sulfones hold a prominent position. The double aza‐analogues of sulfones, sulfondiimines, offer signi…
View article: Friedel–Crafts Reactivity with Sulfondiimidoyl Fluorides for the Synthesis of Heteroaryl Sulfondiimines
Friedel–Crafts Reactivity with Sulfondiimidoyl Fluorides for the Synthesis of Heteroaryl Sulfondiimines Open
Sulfur functional groups are ubiquitous in molecules used in the pharmaceutical and agrochemical industries, and within these collections sulfones hold a prominent position. The double aza‐analogues of sulfones, sulfondiimines, offer signi…
View article: Palladium-Catalyzed Addition of Aryl Halides to <i>N</i>-Sulfinylamines for the Synthesis of Sulfinamides
Palladium-Catalyzed Addition of Aryl Halides to <i>N</i>-Sulfinylamines for the Synthesis of Sulfinamides Open
Sulfinamides are versatile, synthetically useful intermediates, and final motifs. Traditional methods to synthesize sulfinamides generally require substrates with preinstalled sulfur centers. However, these precursors have limited commerci…
View article: Sandmeyer Chlorosulfonylation of (Hetero)Aromatic Amines Using DABSO as an SO<sub>2</sub> Surrogate
Sandmeyer Chlorosulfonylation of (Hetero)Aromatic Amines Using DABSO as an SO<sub>2</sub> Surrogate Open
Sulfonyl chlorides not only play a crucial role in protecting group chemistry but also are important starting materials in the synthesis of sulfonamides, which are in-demand motifs in drug discovery chemistry. Despite their importance, the…
View article: Exploiting <i>trans</i>‐Sulfinylation for the Synthesis of Diverse <i>N</i>‐Alkyl Sulfinamides via Decarboxylative Sulfinamidation
Exploiting <i>trans</i>‐Sulfinylation for the Synthesis of Diverse <i>N</i>‐Alkyl Sulfinamides via Decarboxylative Sulfinamidation Open
Combining simple amines with the bench‐stable sulfinylamine Tr‐NSO allows in situ preparation of reactive alkyl sulfinylamines, which when combined with alkyl radicals generated by photocatalytic decarboxylation, provides N‐alkyl sulfinami…
View article: Exploiting <i>trans</i>‐Sulfinylation for the Synthesis of Diverse <i>N</i>‐Alkyl Sulfinamides via Decarboxylative Sulfinamidation
Exploiting <i>trans</i>‐Sulfinylation for the Synthesis of Diverse <i>N</i>‐Alkyl Sulfinamides via Decarboxylative Sulfinamidation Open
Combining simple amines with the bench‐stable sulfinylamine Tr‐NSO allows in situ preparation of reactive alkyl sulfinylamines, which when combined with alkyl radicals generated by photocatalytic decarboxylation, provides N‐alkyl sulfinami…
View article: The Modular Synthesis of Sulfondiimidoyl Fluorides and their Application to Sulfondiimidamide and Sulfondiimine Synthesis
The Modular Synthesis of Sulfondiimidoyl Fluorides and their Application to Sulfondiimidamide and Sulfondiimine Synthesis Open
A modular synthesis of sulfondiimidoyl fluorides—the double aza‐analogues of sulfonyl fluorides—allowing variation of the carbon and both nitrogen‐substituents is reported. The chemistry uses readily available organometallic reagents, comm…
View article: The Modular Synthesis of Sulfondiimidoyl Fluorides and their Application to Sulfondiimidamide and Sulfondiimine Synthesis
The Modular Synthesis of Sulfondiimidoyl Fluorides and their Application to Sulfondiimidamide and Sulfondiimine Synthesis Open
A modular synthesis of sulfondiimidoyl fluorides—the double aza‐analogues of sulfonyl fluorides—allowing variation of the carbon and both nitrogen‐substituents is reported. The chemistry uses readily available organometallic reagents, comm…
View article: Copper-Catalyzed Synthesis of Masked (Hetero)Aryl Sulfinates
Copper-Catalyzed Synthesis of Masked (Hetero)Aryl Sulfinates Open
Catalysis using substoichiometric copper facilitates the synthesis of masked (hetero)aryl sulfinates under mild, base-free conditions from aryl iodides and the commercial sulfonylation reagent sodium 1-methyl 3-sulfinopropanoate (SMOPS). T…
View article: CCDC 2209822: Experimental Crystal Structure Determination
CCDC 2209822: 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: Photocatalytic Carboxylate to Sulfinamide Switching Delivers a Divergent Synthesis of Sulfonamides and Sulfonimidamides
Photocatalytic Carboxylate to Sulfinamide Switching Delivers a Divergent Synthesis of Sulfonamides and Sulfonimidamides Open
sulfinamides, sulfonamides, and sulfonimidamides are in-demand motifs in medicinal chemistry, yet methods for the synthesis of alkyl variants that start from simple, readily available feedstocks are scarce. In addition, bespoke syntheses o…
View article: Assessing parallel path cooling tower performance via artificial neural networks
Assessing parallel path cooling tower performance via artificial neural networks Open
View article: Crafting chemical space with sulfur functional groups
Crafting chemical space with sulfur functional groups Open
Two synthetic routes to sulfondiimidamides have recently been reported. The ability to prepare and manipulate sulfondiimidamides, which are the double aza-analogs of sulfonamides, in an efficient and predictable way, opens new possibilitie…
View article: CCDC 2091909: Experimental Crystal Structure Determination
CCDC 2091909: 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: Calculation of Nuclear Reactor Cooling Tower Performance With Limited Data Streams
Calculation of Nuclear Reactor Cooling Tower Performance With Limited Data Streams Open
Monitoring of cooling tower performance in a nuclear reactor facility is necessary to ensure safe operation; however, instrumentation for measuring performance characteristics can be difficult to install and may malfunction or break down o…
View article: Modular Two-Step Route to Sulfondiimidamides
Modular Two-Step Route to Sulfondiimidamides Open
Sulfur functional groups are common motifs in bioactive molecules. Sulfonamides are most prevalent but related aza-derivatives, in which oxygen atoms are replaced by imidic nitrogens, such as sulfoximines and sulfonimidamides, are gaining …
View article: Photocatalytic Late-Stage Functionalization of Sulfonamides via Sulfonyl Radical Intermediates
Photocatalytic Late-Stage Functionalization of Sulfonamides via Sulfonyl Radical Intermediates Open
A plethora of drug molecules and agrochemicals contain the sulfonamide functional group. However, sulfonamides are seldom viewed as synthetically useful functional groups. To confront this limitation, a late-stage functionalization strateg…
View article: Domain-Informed Assessment of Nuclear Reactor Operations.
Domain-Informed Assessment of Nuclear Reactor Operations. Open
View article: Sulfondiimidamides as new functional groups for synthetic and medicinal chemistry
Sulfondiimidamides as new functional groups for synthetic and medicinal chemistry Open
Due to their three-dimensional structure, chemical and metabolic stability, polarity, and hydrogen-bonding ability, sulfonamides occupy a privileged position among the functional groups used to design bioactive molecules. The mono aza vari…
View article: Reductant‐Free Cross‐Electrophile Synthesis of Di(hetero)arylmethanes by Palladium‐Catalyzed Desulfinative C−C Coupling
Reductant‐Free Cross‐Electrophile Synthesis of Di(hetero)arylmethanes by Palladium‐Catalyzed Desulfinative C−C Coupling Open
An efficient Pd‐catalyzed one‐pot desulfinative cross‐coupling to access medicinally relevant di(hetero)arylmethanes is reported. The method is reductant‐free, and involves a sulfinate transfer reagent and a Pd‐catalyst mediating the union…
View article: Reductant‐Free Cross‐Electrophile Synthesis of Di(hetero)arylmethanes by Palladium‐Catalyzed Desulfinative C−C Coupling
Reductant‐Free Cross‐Electrophile Synthesis of Di(hetero)arylmethanes by Palladium‐Catalyzed Desulfinative C−C Coupling Open
An efficient Pd‐catalyzed one‐pot desulfinative cross‐coupling to access medicinally relevant di(hetero)arylmethanes is reported. The method is reductant‐free, and involves a sulfinate transfer reagent and a Pd‐catalyst mediating the union…
View article: A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides
A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides Open
A new N-silyl sulfinylamine reagent allows the rapid preparation of a broad range of (hetero)aryl, alkenyl, and alkyl primary sulfinamides, using Grignard, organolithium, or organozinc reagents to introduce the carbon fragment. Trea…
View article: CCDC 2091913: Experimental Crystal Structure Determination
CCDC 2091913: Experimental Crystal Structure Determination Open
View article: CCDC 2091915: Experimental Crystal Structure Determination
CCDC 2091915: Experimental Crystal Structure Determination Open