Simon B. Blakey
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View article: Development of a Diastereoselective Csp<sup>2</sup>–Csp<sup>3</sup> Cross-Coupling Reaction Inspired by Macrocyclic RiPP Natural Products
Development of a Diastereoselective Csp<sup>2</sup>–Csp<sup>3</sup> Cross-Coupling Reaction Inspired by Macrocyclic RiPP Natural Products Open
Macrocyclic peptides containing C(sp2)-C(sp3) side chain cross-links are a rapidly growing subclass of ribosomally synthesized and post-translationally modified peptides (RiPPs), with significant potential in the development of new pharmac…
View article: Enantioselective 3,4-Oxyamination of 1,3-Dienes Enabled by an Electron-Rich Planar Chiral Rhodium Indenyl Catalyst
Enantioselective 3,4-Oxyamination of 1,3-Dienes Enabled by an Electron-Rich Planar Chiral Rhodium Indenyl Catalyst Open
We describe the development of a three-component enantioselective 3,4-amino oxygenation protocol for 1,3-dienes enabled by a highly methylated electron-rich planar chiral rhodium indenyl catalyst. This transformation furnishes vicinal amin…
View article: Discovery and Development of an Aerobic Radical Hydroxyarylation Reaction Using Aryl Halides, Olefins, and O<sub>2</sub>
Discovery and Development of an Aerobic Radical Hydroxyarylation Reaction Using Aryl Halides, Olefins, and O<sub>2</sub> Open
Herein, we report the development of a radical hydroxyarylation reaction through the coupling of an aryl radical, an olefin, and O2. Photoredox activation of a silyl radical halogen atom abstractor enables mild aryl radical generation and …
View article: A One Carbon Linchpin for Rh(III)-Catalyzed, C(sp3)-Directed C–H Annulation
A One Carbon Linchpin for Rh(III)-Catalyzed, C(sp3)-Directed C–H Annulation Open
We disclose a new platform for C(sp3)-directed C–H annulations to generate valuable heterocycles from readily available starting materials. A commercially available one carbon linchpin is leveraged to access alkyl boron species from simple…
View article: Chemical Modifications to Enhance the Drug Properties of a VIP Receptor Antagonist (ANT) Peptide
Chemical Modifications to Enhance the Drug Properties of a VIP Receptor Antagonist (ANT) Peptide Open
Antagonist peptides (ANTs) of vasoactive intestinal polypeptide receptors (VIP-Rs) are shown to enhance T cell activation and proliferation in vitro, as well as improving T cell-dependent anti-tumor response in acute myeloid leukemia (AML)…
View article: Photoredox-Driven Three-Component Coupling of Aryl Halides, Olefins, and O<sub>2</sub>
Photoredox-Driven Three-Component Coupling of Aryl Halides, Olefins, and O<sub>2</sub> Open
Modern organic synthesis requires methodologies that bring together abundant feedstock chemicals in a mild and efficient manner. To aid in this effort, we have developed a multicomponent radical hydroxyarylation reaction that utilizes aryl…
View article: Enantioselective Aziridination of Unactivated Terminal Alkenes Using a Planar Chiral Rh(III) Indenyl Catalyst
Enantioselective Aziridination of Unactivated Terminal Alkenes Using a Planar Chiral Rh(III) Indenyl Catalyst Open
Chiral aziridines are important structural motifs found in natural products and various target molecules. They serve as versatile building blocks for the synthesis of chiral amines. While advances in catalyst design have enabled robust met…
View article: Photoredox-Driven Three-Component Coupling of Aryl Halides, Olefins, and O2
Photoredox-Driven Three-Component Coupling of Aryl Halides, Olefins, and O2 Open
Modern organic synthesis requires methodologies that bring together abundant, feedstock chemicals in a mild and efficient manner. To aid in this effort, we have developed a multicomponent radical hydroxyarylation reaction that utilizes ary…
View article: Enantioselective Aziridination of Unactivated Terminal Alkenes Using a Planar Chiral Rh(III) Indenyl Catalyst
Enantioselective Aziridination of Unactivated Terminal Alkenes Using a Planar Chiral Rh(III) Indenyl Catalyst Open
Chiral aziridines are important structural motifs found in natural products and various important target molecules. They serve as versatile building blocks for the synthesizing chiral amines. While advances in catalyst design have enabled …
View article: Defluoroalkylation of Trifluoromethylarenes with Hydrazones: Rapid Access to Benzylic Difluoroarylethylamines
Defluoroalkylation of Trifluoromethylarenes with Hydrazones: Rapid Access to Benzylic Difluoroarylethylamines Open
Here, we report an efficient and modular approach toward the formation of difluorinated arylethylamines from simple aldehyde-derived N,N-dialkylhydrazones and trifluoromethylarenes (CF3-arenes). This method relies on selective C-F bond cle…
View article: Synthesis, stereochemical assignment, and enantioselective catalytic activity of late transition metal planar chiral complexes
Synthesis, stereochemical assignment, and enantioselective catalytic activity of late transition metal planar chiral complexes Open
Planer chiral complexes emerge as powerful tools for enantioselective catalysis.
View article: Synthesis of Ribosomally Synthesized and Post-Translationally Modified Peptides Containing C–C Cross-Links
Synthesis of Ribosomally Synthesized and Post-Translationally Modified Peptides Containing C–C Cross-Links Open
Ribosomally synthesized and post-translationally modified peptides (RiPPs) are known for their macrocyclic structures, which impart unique biological activity. One rapidly emerging subclass of RiPP natural products contains macrocyclic C-C…
View article: Switchable Regioselective 6-<i>endo</i> or 5-<i>exo</i> Radical Cyclization via Photoredox Catalysis
Switchable Regioselective 6-<i>endo</i> or 5-<i>exo</i> Radical Cyclization via Photoredox Catalysis Open
Controlling the regioselectivity of radical cyclizations to favor the 6-endo mode over its kinetically preferred 5-exo counterpart is difficult without introducing substrate prefunctionalization. To address this challenge, we have develope…
View article: The Mechanism of Rhodium-Catalyzed Allylic C–H Amination
The Mechanism of Rhodium-Catalyzed Allylic C–H Amination Open
Herein, the mechanism of catalytic allylic C-H amination reactions promoted by Cp*Rh complexes is reported. Reaction kinetics experiments, stoichiometric studies, and DFT calculations demonstrate that the allylic C-H activation to generate…
View article: CCDC 1899791: Experimental Crystal Structure Determination
CCDC 1899791: 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: CCDC 1899790: Experimental Crystal Structure Determination
CCDC 1899790: 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: C–H Functionalization Approach for the Synthesis of Chiral C2 Symmetric 1,5-Cyclooctadienes Ligands
C–H Functionalization Approach for the Synthesis of Chiral C2 Symmetric 1,5-Cyclooctadienes Ligands Open
Chiral cyclooctadiene (COD) derivatives are readily prepared by rhodium-catalyzed allylic C-H functionalization of COD. Either mono or difunctionalization of COD is possible generating the products in high yield, diastereoselectivity and e…
View article: C–H Functionalization Approach for the Synthesis of Chiral C2 Symmetric 1,5-Cyclooctadienes Ligands
C–H Functionalization Approach for the Synthesis of Chiral C2 Symmetric 1,5-Cyclooctadienes Ligands Open
Chiral cyclooctadiene (COD) derivatives are readily prepared by rhodium-catalyzed allylic C-H functionalization of COD. Either mono or difunctionalization of COD is possible generating the products in high yield, diastereoselectivity and e…
View article: The Mechanism of Rhodium Catalyzed Allylic C–H Amination
The Mechanism of Rhodium Catalyzed Allylic C–H Amination Open
The mechanism of catalytic allylic C–H amination reactions promoted by Cp*Rh complexes is reported. Reaction kinetics experiments, stoichiometric studies, and DFT calculations demonstrate that allylic C–H activation to generate a Cp*Rh(π-a…
View article: The Mechanism of Rhodium Catalyzed Allylic C–H Amination
The Mechanism of Rhodium Catalyzed Allylic C–H Amination Open
The mechanism of catalytic allylic C–H amination reactions promoted by Cp*Rh complexes is reported. Reaction kinetics experiments, stoichiometric studies, and DFT calculations demonstrate that allylic C–H activation to generate a Cp*Rh(π-a…
View article: Model Studies for the Total Synthesis of 11-Demethoxymyrtoidine and Myrtoidine
Model Studies for the Total Synthesis of 11-Demethoxymyrtoidine and Myrtoidine Open
The malagasy alkaloids, isolated in the 1990s from Madagascan shrub Strychnos myrtoides, are a family of strychnos alkaloids whose members have been reported to potentiate chloroquine activity against resistant strains of Plasmodium falcip…
View article: Recent Developments in C–H Activation for Materials Science in the Center for Selective C–H Activation
Recent Developments in C–H Activation for Materials Science in the Center for Selective C–H Activation Open
Organic electronics is a rapidly growing field driven in large part by the synthesis of π-conjugated molecules and polymers. Traditional aryl cross-coupling reactions such as the Stille and Suzuki have been used extensively in the synthesi…
View article: CCDC 1515996: Experimental Crystal Structure Determination
CCDC 1515996: 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: Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry
Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry Open
A stereoselective cascade annulation reaction generates the tetracyclic core of the Malagasy alkaloids, facilitating the total synthesis of malagashanine.
View article: Iridium(<scp>iii</scp>)-bis(imidazolinyl)phenyl catalysts for enantioselective C–H functionalization with ethyl diazoacetate
Iridium(<span>iii</span>)-bis(imidazolinyl)phenyl catalysts for enantioselective C–H functionalization with ethyl diazoacetate Open
The intermolecular enantioselective C–H functionalization with acceptor-only metallocarbenes is reported using a new family of Ir(iii)-bis(imidazolinyl)phenyl catalysts.
View article: CCDC 1408224: Experimental Crystal Structure Determination
CCDC 1408224: 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: CCDC 1436717: Experimental Crystal Structure Determination
CCDC 1436717: 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 …