Arylboronate esters bearing methyl groups in both of their ortho positions were stably incorporated into lipid membranes at high concentrations without undergoing hydrolysis to the corresponding boronic acids. This method could be used in combination with previous methods to increase the maximum ratio of boron atoms in liposomal boron carriers.
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http://dx.doi.org/10.1039/c6ob02142e | DOI Listing |
J Org Chem
January 2025
Department of Chemistry, Jadavpur University, Kolkata 700032, India.
We have developed a novel protocol for carbonylative homocoupling of arylboronic acids using dithiocarbamate esters as the carbonyl alternative. A series of arylboronic acids underwent smooth reaction with dithiocarbamate ester (MeNCSMe) in the presence of Pd(PPh)Cl catalyst, Cu(OAc)·HO additive, and NaCO in DCE solvent, producing the biaryl ketones efficiently. The mechanism has been studied with the help of several control experiments that reveal the probability of thioamide intermediacy.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Sauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric OptoElectronic Materials, College of Chemistry and Molecular Sciences and The Institute for Advanced Studies and TaiKang Center for Life and Medical Sciences, Wuhan University, 430072, Wuhan, China.
Herein, we describe a practical Borono-Catellani strategy for the efficient synthesis of -aryl glycosides, with readily available arylboronic esters and glycosyl chlorides as the building blocks. It features mild reaction conditions, excellent diastereoselectivities, and good functional group tolerance. A diverse array of highly decorated -(hetero)aryl glycosides are obtained in a convergent and redox-neutral manner.
View Article and Find Full Text PDFJ Am Chem Soc
November 2024
Department of Chemistry, The University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada.
Several recent reports suggest that arylboronic esters can exhibit room temperature phosphorescence (RTP), an optical property that is desirable for applications in security printing, oxygen sensing, and bioimaging. These findings challenged the fundamental notion that heavy elements or changes in orbital symmetry were required for intersystem crossing to occur in organic compounds. As we had not observed long afterglow in the many arylboronic esters we had synthesized over many years, we suspected that the RTP observed in these systems had a simpler explanation: the materials reported were impure.
View Article and Find Full Text PDFJACS Au
October 2024
Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8526, Japan.
The indispensability of a base in Suzuki-Miyaura coupling (SMC) employing organoboronic acids/esters is well recognized, which occasionally induces competitive protodeborylation in organoboron reagents. This phenomenon is particularly pronounced in fluorine-substituted aryl and heteroaryl boron compounds. Here, we show that direct SMC of naphthalene-1,8-diaminato (dan)-substituted aryl boron compounds, Ar-B(dan), characterized by its remarkable stability toward protodeborylation due to their diminished boron-Lewis acidity, occurs utilizing a weak base in conjunction with a palladium/copper cooperative catalyst system.
View Article and Find Full Text PDFMolecules
August 2024
Department of Chemistry and Biochemistry, Graduate School of Humanities and Sciences, Ochanomizu University, 2-1-1, Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan.
The general synthesis of boron-containing cyclic compounds (boracycles) necessitates toxic organotin precursors or highly reactive boron halides. Here, we report the synthesis of seven- and five-membered boracycles utilizing arylboronic acid pinacol esters (ArBpins) as stable boron sources. Grignard reagents generated from 2,2'-dibromodibenzyl or 2,2'-dibromobiphenyl reacted with ArBpins, where Ar = 9-anthryl (Anth), 2,4,6-trimethylphenyl (Mes), or 2,4,6-triisopropylphenyl (Tip), to give 10,11-dihydro-5-dibenzo[,]borepins or dibenzoborole derivatives.
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