Cited by Application of Biaryl Phosphacycles in Palladium‐Catalysed Suzuki‐Miyaura Cross‐Coupling Reactions of Aryl Chlorides

Aryl Acid-Alcohol Cross-Coupling: C(sp³)–C(sp²) Bond Formation from Nontraditional Precursors DOI

Eva Lin,

Johnny Wang,

Edna Mao

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 23, 2025

Alcohols and aryl carboxylic acids are among the most commercially abundant, synthetically versatile, operationally convenient building blocks in organic chemistry. Despite their widespread availability, direct formation of C(sp3)-C(sp2) bonds from these functional groups remains a challenge. Recently, our group developed robust protocols to harness alcohols as alkyl radical precursors, but activation relatively unexplored. Herein, we describe merger N-heterocyclic carbene (NHC)-mediated deoxygenation nickel-mediated decarbonylation toward bond formation. The utility this method is demonstrated through synthesis diverse range aryl-alkyl cross-coupled products late-stage functionalization complex molecules, including drugs, natural products, biomolecules.

Language: Английский

Citations

Synthesis of ortho-arylated and alkenylated benzamides by palladium-catalyzed denitrogenative cross-coupling reactions of 1,2,3-benzotriazin-4(3H)-ones with organoboronic acids DOI

Madasamy Hari Balakrishnan,

Kanagaraj Madasamy,

V. Kasi Sankar

et al.

New Journal of Chemistry, Journal Year: 2021, Volume and Issue: 45(37), P. 17190 - 17195

Published: Jan. 1, 2021

An efficient palladium-catalyzed denitrogenative cross-coupling reaction of 1,2,3-benzotriazin-4(3 H )-ones with organoboronic acids is described. The affords various ortho -aryl and alkenylated benzamides in good to high yields.

Language: Английский

Citations

Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls DOI

Alejandro Cervantes‐Reyes,

Aaron Smith, Gary M. Chinigo

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(8), P. 1678 - 1683

Published: Feb. 24, 2022

Heteroaromatic biaryls are core scaffolds found in a plethora of pharmaceuticals; however, their direct synthesis by the Suzuki cross-coupling is limited to heteroaromatic halide starting materials. Here, we report diverse nitrogen-containing Pd-catalyzed decarbonylative widely available heterocyclic carboxylic acids with arylboronic acids. The practical and modular nature this enabled straightforward preparation >45 heterobiaryl products using pyridines, pyrimidines, pyrazines, quinolines excellent yields. We anticipate that protocol will find broad application medicinal chemistry drug discovery research.

Language: Английский

Citations

Catalytic chemo and homoselective ipso-nitration under mild condition DOI

Hassan Sepehrmansourie,

Mahmoud Zarei, Mohammad Ali Zolfigol

et al.

Molecular Catalysis, Journal Year: 2022, Volume and Issue: 531, P. 112634 - 112634

Published: Sept. 18, 2022

Language: Английский

Citations

Transition metal-catalyzed arylation of unstrained C–C single bonds DOI

Yang Long,

Wuxin Zhou,

Qiang Li

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(45), P. 9809 - 9828

Published: Jan. 1, 2021

Carbon–carbon bond activation is one of the most challenging and important research areas in organic chemistry.

Language: Английский

Citations

Design of Experimental Conditions with Machine Learning for Collaborative Organic Synthesis Reactions Using Transition-Metal Catalysts DOI

Tomoya Ebi,

Abhijit Sen,

Raghu Nath Dhital

et al.

ACS Omega, Journal Year: 2021, Volume and Issue: 6(41), P. 27578 - 27586

Published: Oct. 5, 2021

To improve product yields in synthetic reactions, it is important to use appropriate catalysts. In this study, we used machine learning design catalysts for a reaction system which both Buchwald-Hartwig-type and Suzuki-Miyaura-type cross-coupling reactions proceed simultaneously. First, using an existing dataset, yield prediction models were constructed with between experimental conditions, including the substrate catalyst of two products. Seven methods calculating descriptors proposed, predictive ability was discussed terms methods. Then, predict compound new combinations substrates catalysts, predictions experimentally validated high reproducibility, confirming that can from conditions accuracy. addition, will our added datasets collected scientific papers designed ligands. The proposed candidates tested actual experiments, results exceeded yields.

Language: Английский

Citations

Evaluation of P-bridged biaryl phosphine ligands in palladium-catalysed Suzuki–Miyaura cross-coupling reactions DOI

Jairus L. Lamola, Paseka T. Moshapo,

Cedric W. Holzapfel

et al.

RSC Advances, Journal Year: 2021, Volume and Issue: 11(43), P. 26883 - 26891

Published: Jan. 1, 2021

A family of biaryl phosphacyclic ligands derived from phobane and phosphatrioxa-adamantane frameworks is described. The rigid phosphacycles are efficient for Suzuki-Miyaura cross-coupling aryl bromides chlorides. In particular, coupling reactions the challenging sterically hindered heterocyclic substrates were viable at room temperature.

Language: Английский

Citations

Photothermally induced decarbonylative C H arylation of arenes with aldehydes DOI

Zhenyuan Lin,

Huahui Wang,

WU Qing-hua

et al.

Journal of Catalysis, Journal Year: 2023, Volume and Issue: 426, P. 96 - 100

Published: July 10, 2023

Language: Английский

Citations

Ni/Pd-catalyzed Suzuki–Miyaura cross-coupling of alcohols and aldehydes and C–N cross-coupling of nitro and amines via domino redox reactions: base-free, hydride acceptor-free DOI

Milad Kazemnejadi,

Rebin Omer Ahmed,

Boshra Mahmoudi

et al.

RSC Advances, Journal Year: 2020, Volume and Issue: 10(72), P. 43962 - 43974

Published: Jan. 1, 2020

Domino oxidation-Suzuki-Miyaura cross-coupling of benzyl alcohols with phenylboronic acid and domino reduction-C-N the nitro compounds aryl halides were carried out using a strong Ni/Pd bimetallic redox catalyst. The catalyst bearing copolymer two coordinated metals in porphyrin (derived from demetalated chlorophyll b) salen-type ligands, pyridine moiety as base functionality all immobilized on magnetite NPs was synthesised characterized. oxidation reaction accomplished under molecular O2 absence any hydride acceptor or/and base. Also, reduction C-N performed presence NaBH4 without need for co-reductant. This multifunctional gave moderate to good yields both coupling reactions high chemoselectivity. A wide investigation conducted determine its mechanism

Language: Английский

Citations

Formation of C(sp2)–C(sp3) Bonds Instead of Amide C–N Bonds from Carboxylic Acid and Amine Substrate Pools by Decarbonylative Cross-Electrophile Coupling DOI

Jiang Wang, Lauren E. Ehehalt, Zhidao Huang

et al.

Published: March 15, 2023

Carbonheteroatom bonds, most often amide and ester are the standard method to link together two complex fragments be-cause carboxylic acids, amines, alcohols ubiquitous reactions reliable. However, CN CO linkages a metabolic liability because they prone hydrolysis. While C(sp2)–C(sp3) preferable in many cases, methods make them require different starting materials or less functional-group compatible. We show here new, decarbonylative reaction that forms bonds from of activated acids (via 2-pyridyl esters) with alkyl groups derived amines N-alkyl pyridinium salts) halides). Key this process is remarkably fast, reversible oxidative addi-tion/decarbonylation sequence enabled by pyridone bipyridine ligands that, under conditions purge CO(g), lead selective reaction. The mild enough allow coupling more fragments, such as those used drug develop-ment, demonstrated typical Proteolysis Targeting Chimera (PROTAC) anchor common linkers via CC linkages.

Language: Английский

Citations