Ligand-free Suzuki–Miyaura cross-coupling with low Pd content: rapid development by a fluorescence-based high-throughput screening method

Abstract

Highly efficient ligand-free Suzuki–Miyaura cross-coupling in aqueous solvent at room temperature was developed using metal oxides with low Pd content via a fluorescence-based high-throughput screening method.

Dual-Bioorthogonal Catalysis by a Palladium Peptide Complex

“…To also investigate the catalytic ability of the metallopeptides to mediate the Suzuki–Miyaura cross-coupling reaction, a fluorescence-based catalytic study was performed. The chemosensor 4-bromo- N - n -butyl-1,8-naphthalimide ( HNIBr , 100 μM) was incubated in the presence of phenylboronic acid (PBA, 100 μM) and Pd-peptides 1-Pd and 2-Pd (Pd concentrations of 50 and 60 μM, respectively) in PBS (37 °C, pH 7.4). Fluorescence signal of N - n -hexyl-4-phenyl-1,8-naphthalimide was detected at 460 nm upon ligation of previous building blocks by Pd-peptides 1-Pd and 2-Pd , while no fluorescence increase was shown for L1-Pd and L2-Pd complexes (Figure a,b).…”

Engineering naphthalimide-cyanine integrated near-infrared dye into ROS-responsive nanohybrids for tumor PDT/PTT/chemotherapy

“…ML880 was synthesized through a five-step route ( Scheme 1 A). The commercial compound 4-bromo-1,8-naphthalene anhydride was first substituted by n-butylamine, obtaining compound ML-1 [ [25] , [26] , [27] ]. ML-1 was then reacted with hydrazine hydrate to obtain compound ML-2 [ 28 ], followed by Fischer indole synthesis to obtain compound ML-3 [ 29 ].…”

Rapid Identification of Enamine‐based Organocatalysts for Quaternary Carbon‐containing Aldol Reactions via Fluorescence‐based Screening

“…[5] However, there are few examples of direct monitoring of carbon-carbon bond transformations, such as bond cleavage reactions in retro aldol reactions, [6] bond-forming reactions in Michael reactions, [7] Mannich reactions, [8] olefin metatheses, [9] and coupling reactions. [10] A fluorescent sensor capable of detecting carbon-carbon bond-forming reactions is indispensable for the development of a rapid screening system; in particular, a carbonyl-type sensor has great potential demand owing to its high versatility. Previously, Tanaka and Barbas et al developed an aldehyde-type OFF-ON fluorescence sensor, which they used to detect aldol [11] and allylation [12] reactions.…”