Themed collection p-Block Lewis Acids in Organic Synthesis

16 items
Editorial

Introduction to p-block Lewis acids in organic synthesis

Guest editor Douglas Stephan introduces the Organic & Biomolecular Chemistry p-Block Lewis Acids in Organic Synthesis themed collection.

Graphical abstract: Introduction to p-block Lewis acids in organic synthesis
From the themed collection: p-Block Lewis Acids in Organic Synthesis
Review Article

Synthesis and reactivity of alkynyl boron compounds

Alkynyl boron compounds have attracted profound interest in synthetic organic chemistry. This review article summarizes the various methods developed for the synthesis and reactivity of alkynyl boron compounds in a chronological manner.

Graphical abstract: Synthesis and reactivity of alkynyl boron compounds
From the themed collection: p-Block Lewis Acids in Organic Synthesis
Open Access Review Article

Reactions promoted by hypervalent iodine reagents and boron Lewis acids

Understanding the role of boranes in hypervalent iodine chemistry will open up new reactivities which can be utilised in organic synthesis.

Graphical abstract: Reactions promoted by hypervalent iodine reagents and boron Lewis acids
From the themed collection: p-Block Lewis Acids in Organic Synthesis
Review Article

Tris(pentafluorophenyl)borane catalyzed C–C and C–heteroatom bond formation

This review showcases a collective depiction on the potential utility of BCF as a versatile catalyst to develop various synthetic transformations.

Graphical abstract: Tris(pentafluorophenyl)borane catalyzed C–C and C–heteroatom bond formation
From the themed collection: Editor’s Collection
Communication

Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion

Aldimines and ketimines are hydrosilylated with borenium catalysts at room temperature, giving the corresponding amines in excellent yields. For quinolines, subsequent Mukaiyama aldol reactions can be performed, which are also borenium-ion catalyzed.

Graphical abstract: Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion
From the themed collection: Catalysis & biocatalysis in OBC
Communication

B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines

B(C6F5)3 exhibits high efficiency in tandem protonation/deuteration and reduction of in situ-formed enamines.

Graphical abstract: B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines
From the themed collection: Synthetic methodology in OBC
Communication

FLP-catalysis meets hydrogen-bond activation

The potential of two chiral amidines and three non-chiral boranes in the metal-free hydrogen activation was explored.

Graphical abstract: FLP-catalysis meets hydrogen-bond activation
From the themed collection: p-Block Lewis Acids in Organic Synthesis
Paper

Ligand-free copper-catalyzed borylative defluorination: access to gem-difluoroallyl boronic acid derivatives

We report a ligand-free copper-catalyzed β-borylation, defluorination of β-substituted, α-trifluoromethyl-α,β-unsaturated esters.

Graphical abstract: Ligand-free copper-catalyzed borylative defluorination: access to gem-difluoroallyl boronic acid derivatives
From the themed collection: p-Block Lewis Acids in Organic Synthesis
Paper

An air-stable, Zn2+-based catalyst for hydrosilylation of alkenes and alkynes

An air-stable, Zn2+-based catalyst for catalytic hydrosilylation reactions of alkenes and alkynes.

Graphical abstract: An air-stable, Zn2+-based catalyst for hydrosilylation of alkenes and alkynes
From the themed collection: Catalysis & biocatalysis in OBC
Paper

Formation of amidino-borate derivatives by a multi-component reaction

Amidino-borate derivatives are formed in a five-component reaction between an olefin, three arylisocyanide equivalents and the dimethyl sulfide adduct of the bulky borane (Fmes)BH2.

Graphical abstract: Formation of amidino-borate derivatives by a multi-component reaction
From the themed collection: p-Block Lewis Acids in Organic Synthesis
Open Access Paper

Dibismuthanes in catalysis: from synthesis and characterization to redox behavior towards oxidative cleavage of 1,2-diols

A family of novel dimetallic Bi(III) and Bi(V) complexes is reported. Structural analysis of the complexes in the solid state permitted the study of the Bi–Bi distance and its impact in the catalytic redox properties.

Graphical abstract: Dibismuthanes in catalysis: from synthesis and characterization to redox behavior towards oxidative cleavage of 1,2-diols
From the themed collection: Catalysis & biocatalysis in OBC
Paper

Distiboranes based on ortho-phenylene backbones as bidentate Lewis acids for fluoride anion chelation

We report a new approach to fluorinated distiboranes by reaction of ortho-phenylene distibines with octafluorophenanthra-9,10-quinone. These new derivatives act as bidentate Lewis acids and readily chelate the fluoride anion.

Graphical abstract: Distiboranes based on ortho-phenylene backbones as bidentate Lewis acids for fluoride anion chelation
From the themed collection: p-Block Lewis Acids in Organic Synthesis
Paper

The synthesis, properties, and reactivity of Lewis acidic aminoboranes

A series of aminoboranes were studied to understand their Lewis acidic properties. Unexpectedly, the relative Lewis acidity was dependent on the aromatic nature of the amino substituent and not the B–N bond π-overlap.

Graphical abstract: The synthesis, properties, and reactivity of Lewis acidic aminoboranes
From the themed collection: Synthetic methodology in OBC
Open Access Paper

5-(Diarylimino)- and 5-(sulfoximido)dibenzothiophenium triflates: syntheses and applications as electrophilic aminating reagents

A new method has been developed for the synthesis of dibenzothiophenium salts containing diarylimino and sulfoximido substituents. The reactivity of these compounds under photochemical conditions is presented.

Graphical abstract: 5-(Diarylimino)- and 5-(sulfoximido)dibenzothiophenium triflates: syntheses and applications as electrophilic aminating reagents
From the themed collection: p-Block Lewis Acids in Organic Synthesis
Open Access Paper

Controlling selectivity in N-heterocycle directed borylation of indoles

N-Heterocycle directing groups lead to selective borylation of indole at C2 or C7 controlled by heterocycle ring size. With five membered heterocycle directing groups, C2 borylation is disfavoured due to an increased degree of distortion.

Graphical abstract: Controlling selectivity in N-heterocycle directed borylation of indoles
From the themed collection: p-Block Lewis Acids in Organic Synthesis
Paper

Lewis acid-mediated synthesis of mono- and tris-indole adducts from chiral aziridines

Lewis acid-mediated regio- and stereoselective nucleophilic addition of 2- (or) 3-substituted indoles to non-activated aziridine 2-carboxaldehydes afforded mono- and tris-indole adducts.

Graphical abstract: Lewis acid-mediated synthesis of mono- and tris-indole adducts from chiral aziridines
From the themed collection: Synthetic methodology in OBC
16 items

About this collection

This collection, guest edited by Professor Douglas Stephan (University of Toronto) aims to celebrate p-Block Lewis Acids in Organic Synthesis. The scope covers chemistry that exploits p-block elements for synthetic advantage, including catalytic or stoichiometric reactions that are of synthetic utility or potential.

New articles will be added to the collection upon publication. Please return to this page frequently to see the collection grow


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