Andrew D. Bage
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View article: Experimental and Theoretical Investigations of Copper‐Catalyzed Chemo‐, Regio‐, and Stereoselective <i>cis</i> ‐Hydroboration of 1,3‐Enynes
Experimental and Theoretical Investigations of Copper‐Catalyzed Chemo‐, Regio‐, and Stereoselective <i>cis</i> ‐Hydroboration of 1,3‐Enynes Open
The mechanistic details of the chemo‐, regio‐, and stereoselective cis ‐hydroboration of 1,3‐enynes were investigated using X‐ray crystallography, kinetic analysis, and density functional theory (DFT) calculations. The kinetic analysis rev…
View article: Ruthenium‐Catalyzed Azide‐Selenoalkyne Cycloadditions: A Combined Synthetic–Computational Study into Reaction Scope, Mechanism, and Origins of Regioselectivity
Ruthenium‐Catalyzed Azide‐Selenoalkyne Cycloadditions: A Combined Synthetic–Computational Study into Reaction Scope, Mechanism, and Origins of Regioselectivity Open
A ruthenium‐catalyzed azide–alkyne cycloaddition (RuAAC) reaction involving selenoalkynes is reported for the synthesis of selenium‐substituted 1,2,3‐triazole products (26 examples, up to 89% yield). The reaction works well with a wide ran…
View article: Ruthenium-Catalysed Azide-Selenoalkyne Cycloadditions: A Combined Synthetic-Computational Study into Reaction Scope, Mechanism and Origins of Regioselectivity
Ruthenium-Catalysed Azide-Selenoalkyne Cycloadditions: A Combined Synthetic-Computational Study into Reaction Scope, Mechanism and Origins of Regioselectivity Open
A ruthenium-catalysed azide-alkyne cycloaddition (RuAAC) reaction involving selenoalkynes is reported for the synthesis of selenium-substituted 1,2,3-triazole products (26 examples, up to 89% yield). The reaction works well with a wide ran…
View article: Ruthenium-Catalysed Azide-Selenoalkyne Cycloadditions: A Combined Synthetic-Computational Study into Reaction Scope, Mechanism and Origins of Regioselectivity
Ruthenium-Catalysed Azide-Selenoalkyne Cycloadditions: A Combined Synthetic-Computational Study into Reaction Scope, Mechanism and Origins of Regioselectivity Open
A ruthenium-catalysed azide-alkyne cycloaddition (RuAAC) reaction involving selenoalkynes is reported for the synthesis of selenium-substituted 1,2,3-triazole products (26 examples, up to 89% yield). The reaction works well with a wide ran…
View article: Multifaceted Hidden Catalysis Revealed by Mechanistic Analysis of FeBr<sub>3</sub>‐Catalysed Arene Borylation
Multifaceted Hidden Catalysis Revealed by Mechanistic Analysis of FeBr<sub>3</sub>‐Catalysed Arene Borylation Open
Arene borylation reactions provide direct access to aryl organoboranes, including aryl boronic esters. Precious metals, namely Ir, Rh, Pt, remain the go‐to for metal‐catalysed borylation reactions, however, significant efforts have been ex…
View article: Multifaceted Hidden Catalysis Revealed by Mechanistic Analysis of FeBr<sub>3</sub>‐Catalysed Arene Borylation
Multifaceted Hidden Catalysis Revealed by Mechanistic Analysis of FeBr<sub>3</sub>‐Catalysed Arene Borylation Open
Arene borylation reactions provide direct access to aryl organoboranes, including aryl boronic esters. Precious metals, namely Ir, Rh, Pt, remain the go‐to for metal‐catalysed borylation reactions, however, significant efforts have been ex…
View article: Hidden Boron Catalysis: A Cautionary Tale on TMEDA Inhibition
Hidden Boron Catalysis: A Cautionary Tale on TMEDA Inhibition Open
Hidden boron catalysis plagues catalyzed hydroboration reactions, with the "catalyst" acting to mediate the decomposition of HBpin/HBcat to BH3 which is the actual (hidden) catalyst. N,N,N',N'-Tetrame…
View article: Chemo-, Regio-, and Stereoselective <i>cis</i>-Hydroboration of 1,3-Enynes: Copper-Catalyzed Access to (<i>Z,Z</i>)- and (<i>Z,E</i>)-2-Boryl-1,3-dienes
Chemo-, Regio-, and Stereoselective <i>cis</i>-Hydroboration of 1,3-Enynes: Copper-Catalyzed Access to (<i>Z,Z</i>)- and (<i>Z,E</i>)-2-Boryl-1,3-dienes Open
A copper-catalyzed alkyne-selective hydroboration of 1,3-enynes is disclosed, providing access to the previously elusive 2-boryl-1,3-dienes. Using CuOAc, Xantphos, and HBpin, Bpin was installed on the internal carbon of a series of symmetr…
View article: <i>B</i>–N/<i>B</i>–H Transborylation: borane-catalysed nitrile hydroboration
<i>B</i>–N/<i>B</i>–H Transborylation: borane-catalysed nitrile hydroboration Open
The reduction of nitriles to primary amines is a useful transformation in organic synthesis, however, it often relies upon stoichiometric reagents or transition-metal catalysis. Herein, a borane-catalysed hydroboration of nitriles to give …
View article: A Boron-Oxygen Transborylation Strategy for the Asymmetric Reduction of Ketones
A Boron-Oxygen Transborylation Strategy for the Asymmetric Reduction of Ketones Open
The asymmetric reduction of ketones with pinacolborane (HBpin) has been catalysed by an enantioenriched borane catalyst, formed in situ from 9-borabicyclo[3.3.1]nonane (H- B -9-BBN) and β-pinene. While previously only used stoichiometrical…
View article: A Boron-Oxygen Transborylation Strategy for the Asymmetric Reduction of Ketones
A Boron-Oxygen Transborylation Strategy for the Asymmetric Reduction of Ketones Open
The asymmetric reduction of ketones with pinacolborane (HBpin) has been catalysed by an enantioenriched borane catalyst, formed in situ from 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) and β-pinene. While previously only used stoi…
View article: Hidden Boron Catalysis: Nucleophile-Promoted Decomposition of HBpin
Hidden Boron Catalysis: Nucleophile-Promoted Decomposition of HBpin Open
Simple nucleophiles with structural similarities to known hydroboration catalysts can readily mediate the formation of BH3 and borohydride species from pinacolborane (HBpin). Alkyne and alkene hydroboration reactions were succes…
View article: Kinetics and Mechanism of the Arase-Hoshi R<sub>2</sub>BH-Catalyzed Alkyne Hydroboration: Alkenylboronate Generation via B–H/C–B Metathesis
Kinetics and Mechanism of the Arase-Hoshi R<sub>2</sub>BH-Catalyzed Alkyne Hydroboration: Alkenylboronate Generation via B–H/C–B Metathesis Open
The mechanism of R2BH-catalyzed hydroboration of alkynes by 1,3,2-dioxaborolanes has been investigated by in situ 19F NMR spectroscopy, kinetic simulation, isotope entrainment, single-turnover labeling (10B…