The coupling reaction of pinacolborane with various aryl bromides in the presence of a catalytic amount of Pd(OAc)(2) together with DPEphos as ligand and Et(3)N as base provided arylboronates. High yields were obtained in the case of electron-donor substituted aryl bromides. The direct preparation of arylboronates allowed the one-pot, two-step synthesis of unsymmetrical biaryls in high yields. [reaction: see text]
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol048303b | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Transformation-Guided Genome Mining Provides Access to Brominated Lanthipeptides.
Org Lett
January 2025
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.
Natural product biosynthesis is nature's tinkering ground for developing new enzymes that can achieve chemical transformations that are outside the purview of traditional chemical catalysis. Herein we describe a genome mining approach that leads to the discovery of a halogenase that regioselectively brominates a tryptophan side chain indole for a macrocyclic peptide substrate, enabling downstream chemical arylation by Suzuki-Miyaura coupling. The halogenase was found to prefer a macrocyclic peptide substrate over a linear peptide.
View Article and Find Full Text PDFVisible-Light-Induced Synthesis of Esters via a Self-Propagating Radical Reaction.
J Org Chem
January 2025
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China.
We herein disclose a visible-light-induced synthesis of aryl esters through the cross-dehydrogenative coupling of aldehydes with phenols using BrCCl, in which phenolate functions as both a substrate and a photosensitizer. This transition-metal- and photocatalyst-free visible-light-induced esterification is suitable for a wide range of substrates and gives moderate to excellent yields (up to 95%). Mechanistic studies provided evidence of a self-propagating radical reaction involving homolytic cleavage of the aldehydic C-H bond and the formation of acyl bromides.
View Article and Find Full Text PDFSecondary Alkylation of Arenes via the Borono-Catellani Strategy.
J Am Chem Soc
January 2025
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 TaiKang Center for Life and Medical Sciences, Wuhan University, Wuhan 430072, China.
A modular platform technology for the synthesis of α-aryl carbonyl derivatives via Borono-Catellani-type secondary alkylation of arenes is presented. This practical method features a broad substrate scope regarding aryl boronic acid catechol esters, secondary alkyl bromides, and diversified terminating reagents (e.g.
View Article and Find Full Text PDFNickel-catalyzed reductive cross-coupling of difluoromethylated secondary alkyl bromides with organohalides.
Chem Commun (Camb)
January 2025
School of Chemistry and Chemical Engineering, Nanchang University, Nanchang, Jiangxi, 330031, China.
We present a highly efficient and versatile nickel-catalyzed protocol for the reductive cross-coupling of unactivated CFH-substituted electrophiles with a wide variety of aryl and alkenyl halides. This novel approach offers high catalytic reactivity and broad functional group compatibility, enabling late-stage fluoroalkylation of drug molecules.
View Article and Find Full Text PDFRapid and Sustainable Electrochemical Pd Catalyst Generation from Bulk Metal.
Chemistry
January 2025
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, 119991, Moscow, RUSSIAN FEDERATION.
Palladium catalysts form a cornerstone of modern chemistry with upmost scientific and industrial impact. Bulk palladium metal itself is chemically inert, and a sequence of chemical transformations has to be utilized to convert the metal into Pd pre-catalyst covered by ligands. However, the "cocktail" of catalysis concept discovered recently has shown that Pd systems can efficiently operate in catalysis without the necessity of a complicated and expensive pre-installed ligand environment.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!