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Unlocking the Power of “Boronics”: Easy Method for Creating Tertiary Aryl Amines from “Nitros”

Article • Advanced Synthesis & Catalysis

This paper introduces a new three-component chemical process that efficiently transforms inexpensive nitro compounds, boronic acids, and trialkyl phosphites into tertiary aromatic amines. The method is highly versatile, accommodating various chemical groups on nitro and boronic acid components. Its uniqueness lies in not requiring transition-metal catalysts, making it cost-effective and environmentally friendly. Additionally, it can work alongside other metal-catalyzed methods, enabling the synthesis of diverse compounds, including special types like α-amino ester derivatives.

Unlocking a Chemistry's Secret: Nitrosobenzene Unleashes Aldehyde Power for C-H to C-C Conversion

Article • Angewandte Chemie

We've discovered a new way to make ketones, which are important compounds, without using complicated metal-based reactions. Instead, we use nitrosobenzene along with unexpensive aldehydes and boronic acids. In this new method, nitrosobenzene activates the boronic acid and the aldehyde in a way that helps them join together to form ketones. This approach is easy to use on a larger scale and is a practical way to make ketones without the need for complex processes.

Discovering Efficient Cobalt Catalysts for Selective Chemical Reactions

Article • Journal of Catalysis

This research introduces a new and highly effective catalyst that improves a key chemical process used to create vinylsilane compounds, which are important in various fields like organic chemistry. The catalyst works with a wide range of materials and conditions, showing excellent stability and efficiency. It can transform different types of alkynes into useful products with great precision and minimal catalyst needed. This innovative approach offers a more efficient and versatile solution compared to previous methods, opening up new possibilities for producing important chemical compounds.

Eco-Friendly Synthesis of Aminophosphonates with Unique Fluorescence

Article • Angewandte Chemie

We’ve created an environmentally friendly way to make a special type of chemical compound called aminophosphonates without using metals. The resulting compounds have unique light-related properties, which means they can emit light in different ways depending on their structure.

Mono-N-Methyl/Alkyl Amines: Synthesis without overalkylation

Article • ACS Omega

This paper presents an innovative method for the selective synthesis of mono-N-methyl/Alkyl aromatic amines. We address the challenges associated with the synthesis of these compounds, which are common scaffolds in pharmaceutical, dye, and agrochemical compounds.

How to make C–N bonds using boronic acids without transition metals

Article • Chemical Society Reviews

This tutorial review discusses recent advancements in boronic acid-mediated C-N bond-forming reactions (amination, amidation, nitration, and nitrosation) without the need for transition-metals. Emphasizing the less-explored aspect of boronic acids as nucleophiles, it covers reagents and mechanisms. The paper underscores their sustainable role in synthesizing amines, amides, nitroso, and nitro compounds, contributing to eco-friendly approaches in pharmaceuticals, polymers, and materials synthesis.

Making Flufenamic Acid with Boronic Acids & Nitrosoarenes – A Lab Adventure for Chemistry Students

Article • Journal of Chemical Education

NSAIDs in the Battle Against Discomfort: Flufenamic acid is a representative example of nonstereoidal anti-inflammatory drugs (NSAIDs), which are among the best-selling drugs worldwide (there is an estimate of more than 100 million prescriptions per year in the USA alone). The synthesis of best-selling pharmaceutical compounds is one of the most attractive laboratory experiences for chemistry students. This is especially appealing for those enrolled in organic chemistry courses in pharmacy faculties. This paper details an undergraduate organic chemistry experiment focusing on nitroso compounds and boronic acids. Students synthesize nitrosobenzenes, couple them with boronic acids without using transition-metals, and produce flufenamic acid by two different routes that they compare.

Visible‐Light‐Promoted Dearomatization for The Construction of Imidazole Scaffolds

Article • Advanced Synthesis & Catalysis

Diastereoselective reduction of α-acyl-N-[Bis(methylthio)methylene]alaninates and phenylalaninates: Synthesis of α,α-disubstituted β-hydroxy α-amino esters

Article • Tetrahedron

Regioselective Ring-Opening and Cross-Coupling Metathesis of 2-Substituted 7-Oxanorbornenes. New Stereoselective Entry into Trisubstituted Tetrahydrofurans

Article • The Journal of Organic Chemistry

Tetrabutylammonium cyanide catalyzed diasteroselective cyanosilylation of chiral α-hydroxyketones

Article • Tetrahedron

(Ph3P)AuCl-catalyzed homocoupling of arylboronic acids under benchtop conditions: Synthesis of biphenyls

Article • Molecular Catalysis

Metal‐Free Aminophosphonation: Eco‐Friendly Synthesis and Photophysical Properties of Fluorescent 3‐(Aminoimidazo[1,2‐a]Pyridin‐2‐yl)Phosphonates

Article • Angewandte Chemie

Towards understanding the behavior of polyelectrolyte–surfactant mixtures at the water/vapor interface closer to technologically-relevant conditions

Article • Physical Chemistry Chemical Physics

Stereoselective coupling of ketone and carboxylate enolates

Article • Chemical Society Reviews

Transition-metal-free C–C bond forming reactions of aryl, alkenyl and alkynylboronic acids and their derivatives

Article • Chemical Society Reviews

Conjugate addition reactions of carbon nucleophiles to electron-deficient dienes

Article • Chemical Society Reviews

Transition-metal free reactions of boronic acids: cascade addition – ring-opening of furans towards functionalized γ-ketoaldehydes

Article • Chemical Communications

Metal-free ring-opening of epoxides with potassium trifluoroborates

Article • Chemical Communications

Selective Double Bond Reduction in Carbonyl-Conjugated Vinylfurans

Article • Synthetic Communications

Magnesium monoperoxyphtalate: A new reagent for the oxidative ring opening of furans to cis-enediones

Article • Tetrahedron Letters

1,3-Dipolar cycloadditions of benzonitrile oxide to vinyl and azavinyl furan derivatives

Article • Tetrahedron Letters

Synthesis of 2,5-bis-(Ethynyl) furan Derivatives from 2,5-Furandicarboxaldehyde

Article • Synthetic Communications

Chemoselective reduction in carbonyl-conjugated vinylfurans by the Mg/MeOH system

Article • Tetrahedron Letters

New aspects in the regioselective functionalization of furans. synthesis of tri-and tetrasubstituted furan derivatives.

Article • Tetrahedron

Diastereoselective synthesis of functionalized 2,4-diamino-3-hydroxyglutaric acid derivatives of potential biological interest from glycine derivatives

Article • Tetrahedron Letters

Stereochemistry of Silyl Ketene Acetals of Some 8-Phenylmenthyl Arylacetates

Article • The Journal of Organic Chemistry

Diastereoselective Alkylation of 8-Phenylmenthyl Phenylacetate: Aggregated Lithium Enolate versus "Naked" Enolate

Article • The Journal of Organic Chemistry

Diastereoselective Synthesis of Substituted Glutamic Acid Derivatives via Michael Additions of N-[Bis(methylthio)methylene]glycinates under Solid-Liquid Phase Transfer Catalysis

Article • The Journal of Organic Chemistry

Asymmetric Alkylation of 8-Phenylmenthyl N-[Bis(methylthio)methylene]glycinate Enolates. Synthesis of D- and L-.alpha.-Amino Acids from a Single Chiral Precursor

Article • The Journal of Organic Chemistry

Diastereoselective 1,3-dipolar cycloaddition of Sm(III)-azomethine ylides to α,β-unsaturated esters

Article • Tetrahedron Letters

Reaction of N-[bis(methylthio)methylene]glycinates with electron deficient alkynes. Synthesis of (Z)-α,β-didehydroglutamic acid derivatives

Article • Tetrahedron Letters

On the acylation reactions of aza-allyl carbanions derived from N-[bis(methylthio)methylene]glycine ethyl ester and N-[bis(methylthio)methylene]benzylamine

Article • Tetrahedron

Diastereoselective Synthesis of α,α-Disubstituted γ-Carboxypyroglutamates via Sm(III)−Azomethine Ylide Cycloadditions

Article • The Journal of Organic Chemistry

Asymmetric Oxidative Dimerization of the Enolates ofN-[Bis(methylthio)methylene]- andN-(Diphenylmethylene)glycine Esters

Article • The Journal of Organic Chemistry

Diastereoselective Aldol Reactions of ( Z )- N -[Bis(methylthio)methylene]-α,β-didehydroglutamates

Article • The Journal of Organic Chemistry

Study of the asymmetric synthesis of (Z)-γ-substituted α,β-dihehydroglutamates from N-alkylideneglycinates

Article • Tetrahedron

Reaction of α,β-unsaturated ketones with LiAlH4 under oxygen: synthesis of 1,3-diols

Article • Tetrahedron Letters

Diastereoselective synthesis of syn,syn- and syn,anti-2,4-diamino-3-hydroxyglutaric acid derivatives from ethyl α-acyl alaninates

Article • Tetrahedron

Control of the Regioselectivity in the Pauson−Khand Reaction of 7-Oxanorbornene Derivatives

Article • The Journal of Organic Chemistry

Carboxylates as pronucleophiles in the phosphine-catalyzed γ-addition reaction

Article • Tetrahedron Letters

Synthesis of γ,δ-Didehydrohomoglutamates by the Phosphine-Catalyzed γ-Addition Reaction to Acetylenic Esters

Article • The Journal of Organic Chemistry

Synthesis of 1,1′-methylenedi[(1 R ,1′ R ,3 R ,3′ R ,5 R ,5′ R )-8-oxabicyclo[3.2.1]oct-6-en-3-ol] and derivatives: precursors of long-chain polyketides

Article • Tetrahedron Asymmetry

Regioselective domino metathesis of 7-oxanorbornene derivatives as a new stereoselective entry into 2,6-dioxabicyclo[4.3.0]nonenes

Article • Tetrahedron Letters

An expeditious entry to the hydrophenalene ring system of pseudopterosins

Article • Tetrahedron Letters

Regio- and stereoselective ring-opening dimerization–cross-coupling metathesis of 7-oxanorbornene derivatives

Article • Journal of Organometallic Chemistry

Regio- and Stereoselective Addition of Grignard and Organolithium Reagents to 4-Hydroxy-2-cyclopentenones

Article • The Journal of Organic Chemistry

On the Reactivity of (7-Oxabicyclo[2.2.1]hept-5-en-2-ylidene)amines. Different Reaction Paths Leading to the Same Final Products

Article • Helvetica Chimica Acta

First intermolecular Pauson–Khand reaction of 7-azanorbornenes. Control of the regioselectivity by the effect of the substituents attached to the olefinic partner

Article • Tetrahedron Letters

Conformationally restricted glutamic acid derivatives: asymmetric synthesis of 4-substituted 4,5-dihydro-3(2H)-pyridazinones

Article • Tetrahedron Letters

The Staudinger reaction of imines derived from 7-oxanorbornenone: formation of spiranic oxazinone versus β-lactam rings

Article • Tetrahedron Letters

Domino Metathesis of 2-Azanorbornenones:  A New Strategy for the Enatioselective Synthesis of 1-Azabicyclic Compounds

Article • The Journal of Organic Chemistry

Diastereoselective Synthesis and Estimation of the Conformational Flexibility of 6-Oxoperhydropyridazine-3-carboxylic Acid Derivatives

Article • The Journal of Organic Chemistry

Asymmetric C C bond formation by the mixed oxidative coupling of 1,1′-bi-2-naphthyl esters

Article • Tetrahedron Asymmetry

Enantioselective Synthesis of γ,δ-Disubstituted β-Hydroxy δ-Lactones from Furans: Synthesis of (+)-Prelactone B and its C-4 Epimer

Article • Synlett

The reaction of spiroepoxycyclohexadienones towards cyanide nucleophiles

Article • Tetrahedron

Control of product distribution in the domino metathesis reactions of N-alkynyl 2-azabicyclo[2.2.1]hept-5-en-3-ones. A convenient synthesis of functionalized γ-lactams and indolizidinones

Article • Tetrahedron Letters

Asymmetric synthesis of cyclopentenones with benzylic α-quaternary carbon stereogenic centres from furans

Article • Tetrahedron Asymmetry

Stereoselectivity Control in the Rh(I)-Catalyzed Conjugate Additions of Aryl and Alkenylboronic Acids to Unprotected Hydroxycyclopentenones

Article • Organic Letters

Stereoselective Synthesis of Tetrahydrofuran Spiro‐β‐Lactams by Ru‐Catalyzed Metathesis of 7‐Oxabicyclo[2.2.1]heptenes

Article • Helvetica Chimica Acta

Rhodium-Catalyzed Reaction of Aryl- and Alkenylboronic Acids with 2,4-Dienoate Esters:  Conjugate Addition and Heck Reaction Products

Article • Organic Letters

Stereoselective Conjugate Addition of Aryl- and Alkenylboronic Acids to Acyclic γ,δ-Oxygen-Substituted α,β-Enoates

Article • Organic Letters

Benzylic Substitution of Gramines with Boronic Acids and Rhodium or Iridium Catalysts†

Article • Organic Letters

An Efficient Synthesis of Enantiomerically Pure (1R,2S,5S)- and (1S,2R,5R)-Rosaprostol Methyl Esters

Article • Synlett

Stereoselective RhI-Catalyzed Tandem Conjugate Addition of Boronic Acids−Michael Cyclization

Article • Organic Letters

Stereoselective Rhodium-Catalyzed Conjugate Addition of Boronic Acids to Unprotected δ-Hydroxy-γ-butenolides. Synthesis of (−)-7-Oxamuricatacin and β-Substituted Derivatives

Article • The Journal of Organic Chemistry

N-Heterocyclic Carbene-Catalyzed Monoacylation of 1,4-Naphthoquinones with Aldehydes

Article • The Journal of Organic Chemistry

Diastereoselective Synthesis of 1,2,3-Trisubstituted Indanes via Rhodium(I)-Catalyzed Tandem Conjugate Additions

Article • Synthesis

Arylation of Benzo-Fused 1,4-Quinones by the Addition of Boronic Acids under Dicationic Pd(II)-Catalysis

Article • Organic Letters

A Convenient Approach to Polycyclic Derivatives with a cis‐Fused 2,6‐Dioxabicyclo[4.3.0]nonane System by the Sequence Ring‐Opening/Intramolecular Ring‐Closing Enyne Metathesis/Diels–Alder Reaction

Article • European Journal of Organic Chemistry

1,6-Conjugate Addition of Boronic Acids to 2-Allylidenemalonates

Article • Synlett

In vitro antiamyloidogenic properties of 1,4-naphthoquinones

Article • Biochemical and Biophysical Research Communications

Synthesis and evaluation of arylquinones as BACE1 inhibitors, β-amyloid peptide aggregation inhibitors, and destabilizers of preformed β-amyloid fibrils

Article • Bioorganic & Medicinal Chemistry Letters

Regioselective 1,6-Conjugate Addition of Boronic Acids and Grignard Reagents to Dienylpyridines

Article • Synlett

Trifluoroacetic anhydride—catalyzed conjugate addition of boronic acids to α,β-unsaturated ketones

Article • Tetrahedron Letters

Trifluoroacetic Anhydride Promoted Tandem Conjugate Addition of Boronic Acids/Acetal Ring Opening

Article • Organic Letters

Stereoselective Synthesis of Indanylglycine Derivatives by a Tandem Michael–Michael Reaction

Article • Synlett

PdII‐Catalyzed Conjugate Addition of Boronic Acids to Ketoglutaconic Esters toward the Synthesis of Functionalized Pyridazin‐3(2H)‐ones with Neuroprotective Activity

Article • European Journal of Organic Chemistry

Transition-Metal-Free Reactions of Boronic Acids: 1,3-Stereochemical Induction in the Substrate-Controlled Conjugate Addition

Article • The Journal of Organic Chemistry

Discovery of alkenylboronic acids as neuroprotective agents affecting multiple biological targets involved in Alzheimer’s disease

Article • Bioorganic & Medicinal Chemistry Letters

Transition-Metal-Free Direct anti-Carboboration of Alkynes with Boronic Acids To Produce Alkenylheteroarenes

Article • Organic Letters

Metal-Free Conjugate Addition of Alkenylboronic Acids to Enedicarbonyl Compounds towards the Synthesis of Pyridazine Derivatives

Article • Synthesis

1,2‐Stereochemical Induction in the PdII‐Catalyzed Conjugate Addition of Boronic Acids

Article • European Journal of Organic Chemistry

Ring-Opening of Donor–Acceptor Cyclopropanes by Boronic Acids and Potassium Organotrifluoroborates under Transition-Metal-Free Conditions

Article • The Journal of Organic Chemistry

C–C Bond Formation with Boronic Acids and Derivatives by Tran­sition-Metal-Free Conjugate Addition Reactions

Article • Synthesis

Transition-Metal-Free Stereocomplementary Cross-Coupling of Diols with Boronic Acids as Nucleophiles

Article • Organic Letters

Metal-Free Organocatalysis

Article • Catalysts

Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling

Article • Organic Letters

Selective Functionalization of Achmatowicz Rearrangement Products by Reactions with Potassium Organotrifluoroborates under Transition-Metal-Free Conditions

Article • The Journal of Organic Chemistry

Synthesis of Ketones by C−H Functionalization of Aldehydes with Boronic Acids under Transition‐Metal‐Free Conditions

Article • Angewandte Chemie

Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions

Article • Pharmaceuticals

Stereochemistry of the Tetrabutylammonium Cyanide-Catalyzed Cyanosylilation of Cyclic α,β-Epoxyketones – Dependence of the Diastereoselectivity on the Ring Size

Article • European Journal of Organic Chemistry