Aryl Boronic Esters Are Stable on Silica Gel and Reactive under Suzuki–Miyaura Coupling Conditions

Abstract

A wide range of aryl boronic 1,1,2,2-tetraethylethylene glycol esters [ArB­(Epin)­s] were readily synthesized. Purifying aryl boronic esters by conventional silica gel chromatography is generally challenging; however, these introduced derivatives are easily purified on silica gel and isolated in excellent yields. We subjected the purified ArB­(Epin) to Suzuki–Miyaura couplings, which provided higher yields of the desired biaryl products than those obtained using the corresponding aryl boronic acids or pinacol esters.

Construction of Heterobiaryl Skeletons through Pd-Catalyzed Cross-Coupling of Nitroarenes and Heterocyclic Arylborononate Esters with a Sterically Demanding NHC Ligand

“…The presence of heteroaryl groups is particularly pervasive in medicinal chemistry, and thus the coupling reactions of nitroarenes and heteroarylboronic acids deserve further exploration. It has been noted that heteroarylboronic acids are prone to in situ protodeboronation, − and the heteroatom may coordinate with the metal center, leading to the deactivation of the transition metal catalysts . Therefore, the selection of suitable boronate reagents and compatible metal catalysts would be critical to achieve efficient coupling.…”

Acceleration of Nonradiative Charge Recombination Reactions at Larger Distances in Kinked Donor–Bridge–Acceptor Molecules

“…Three kinked BD–Bridge–TPA molecular systems, where Bridge is no additional bridge (NA), phenyl (Ph), and fluorene (F 1 ), were successfully synthesized (Figure c). We used a one-pot, two-step Suzuki coupling for Ph and F 1 bridges, which helps avoid the isolation of the aryl boronic esters …”

“…We used a one-pot, two-step Suzuki coupling for Ph and F 1 bridges, which helps avoid the isolation of the aryl boronic esters. 47 3.2. Observation of CT Emission.…”

Anthranilamide-protected vinylboronic acid: rational monomer design for improved polymerization/transformation ability providing access to conventionally inaccessible copolymers

“…1a). 2 For instance, this protecting-group-dependent reactivity enables the precise synthesis of oligoarenes via iterative Suzuki–Miyaura cross-coupling (SMC) reactions via a detachable masking group such as 1,8-diaminonaphthalene (dan) or N -methyliminodiacetic acid (mida). 3,4 Anthranilamide (aam) is another class of masking group for such coupling reactions; Suginome and co-workers have reported that aam-protected boron moieties act as a directing group for ortho -selective C–H-activation reactions due to the affinity of the amide group toward transition-metal complexes.…”