Recognition of Aromatic Compounds by π Pocket within a Cage‐Shaped Borate Catalyst

Abstract

Taking shape: the ability of a Lewis acid catalyst to distinguish between aromatic and aliphatic hydrocarbon moieties was accomplished by using cage-shaped borate catalysts B(OC(6)H(3)Aryl)(3)CH having a π pocket derived from aryl substituents surrounding the boron center. The catalyst predominantly activated aromatic aldehydes over aliphatic ones for reaction.

Pushing the Lewis Acidity Boundaries of Boron Compounds With Non‐Planar Triarylboranes Derived from Triptycenes

“…Knowing that several free or coordinated non‐planar boron Lewis acids are known, such as borabenzobarrelene 7 (Scheme ), 1‐bora adamantane 8 , and 9 , we have been stimulated to generate the boratriptycene Lewis acid 6 and to design Lewis acid/base bifunctional molecules such as 10 with a B atom and a P atom at each edge of the triptycene framework (Scheme ).…”

Tuning Lewis Acidity by a Transannular pπ–σ* Interaction between Boron and Silicon/Germanium Atoms Supported by a Cage‐Shaped Framework

“…In general, the properties of a metal complex are tuned by replacing its ligand and/or by changing the geometry around the metal center . We recently established the effectiveness of a cage‐shaped triphenolic ligand in controlling the Lewis acidity of a boron atom …”

Structures and Properties of Molecular Torsion Balances to Decipher the Nature of Substituent Effects on the Aromatic Edge‐to‐Face Interaction

“…Noncovalent aromatic–aromatic interactions are pivotal in numerous chemical and biological processes 1. These interactions play a key role in host–guest chemistry,2 supramolecular self‐assembly,3 stereoselective reactions,4 chemoselective catalysis,5 or protein–ligand complexation6 and influence the structure of biomolecules 7. There are three major structural motifs for aryl–aryl interactions: parallel‐eclipsed, parallel‐displaced, and edge‐to‐face (Figure 1).…”