Themed collection 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.

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.

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

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

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.

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

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

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

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

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.

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.

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.

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.

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.

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.

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.