Review
Chemistry, Applied
Ramil Fatykhov, Igor Khalymbadzha, Oleg Chupakhin
Summary: This review article summarizes the C-H/C-H cross-coupling reactions of phenols with heterocyclic compounds and discusses different activation methods. The goal is to inspire increased interest in developing new methodologies in this field.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Kento Asai, Masahiro Miura, Koji Hirano
Summary: A palladium-catalyzed cross-coupling reaction between diarylmethanol derivatives and diborylmethane has been developed, delivering the corresponding homobenzylic boronates in good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xinjie Li, Peng Qi, Hongguang Du
Summary: A metal-free cross-dehydrogenation coupling method was developed for the synthesis of N-9 alkylated purine derivatives. Thioethers were used as versatile alkylation reagents with PhI(OAc)2 as the oxidant, resulting in moderate to good yields. The regioselectivity of this method involving unsymmetrical thioethers and purine derivatives was also investigated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Tomer Mintz, Nagnath Yadav More, Eden Gaster, Doron Pappo
Summary: This study reports a novel iron-catalyzed oxidative cross-coupling reaction between phenols and 3-alkyloxindole derivatives, leading to the synthesis of 3-alkyl-3-(hydroxyaryl)oxindole compounds with high selectivity. The generality of the conditions has been proven and can be applied to various substituted phenols, naphthols, and tyrosine derivatives. Additionally, modifications to the reaction conditions have enabled the conjugation of tyrosine-containing short peptides with oxindolylalanine (Oia) derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Wenbo Ma, Yang Wang, Bo Li, Yunhao Zhou, Yue Xu, Yanan Sun, Linghui Gu, An Cheng
Summary: A Rh(III)-catalyzed direct alkenylation of arenes with readily available vinyltrifluoroborate has been reported. This method allows for the direct synthesis of functionalized styrenes under mild conditions, tolerating a wide range of functional groups with excellent site- and regioselectivity. The utility of the method has been demonstrated through the further transformation of the obtained functionalized styrenes.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Peng Wu, Jas S. Ward, Kari Rissanen, Carsten Bolm
Summary: Copper-catalyzed cross-coupling reactions of alpha-bromoaryl NH-sulfoximines with elemental sulfur were used to synthesize benzo[d][1,3,2]dithiazole-1-oxides, which belong to a new class of three-dimensional heterocycles. The reactions exhibited good functional group and heterocycle tolerance under mild conditions. Moreover, the initial cross-coupling products could be converted to unprecedented cyclic sulfonimidamides derivatives through imination/oxidation. Additionally, a seven-membered heterocycle was obtained by a ruthenium-catalyzed ring-expansion with ethyl propiolate.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Organic
Andryj M. Borys, Eva Hevia
Summary: The Ni-catalysed hydrogenolysis and cross-coupling of aryl ethers is a powerful synthetic tool that can transform inert phenol-derived electrophiles into functionalised aromatic molecules. Although the mechanisms of these reactions are still uncertain, experimental and theoretical investigations have generated knowledge that will facilitate future discoveries in the development of novel Ni-catalysed transformations of aryl ethers.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Xichao Peng, Junhao Zhao, Guojian Ma, Yan Wu, Shiyu Hu, Zhixiong Ruan, Pengju Feng
Summary: The study proposes a sustainable method for the selective synthesis of C-2/C-3 aminated five-membered heteroarenes incorporated with functionalities from aniline derivatives through an electro-oxidative cross coupling process. This approach enables the synthesis of a wide variety of heteroarene derivatives, tolerates functional groups, and is suitable for gram-scale synthesis. Preliminary mechanistic studies suggest a radical cross coupling process between the N-centered radical and indole radical cation may be involved in this amination reaction.
Article
Chemistry, Multidisciplinary
Igor Zayakin, Evgeny Tretyakov, Anna Akyeva, Mikhail Syroeshkin, Julia Burykina, Andrey Dmitrenok, Alexander Korlyukov, Darina Nasyrova, Irina Bagryanskaya, Dmitri Stass, Valentine Ananikov
Summary: Nitronyl nitroxides are important functional building blocks that can be used for molecular-level optimization and nano-scale device development. Efficient synthetic approaches for these compounds are still challenging.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Multidisciplinary Sciences
Peng-Ying Jiang, Kai-Fang Fan, Shaoyu Li, Shao-Hua Xiang, Bin Tan
Summary: The authors present a metal-free oxidative cross-coupling reaction between isoquinolines and 2-naphthols to efficiently access the QUINOL scaffolds. This approach addresses the challenge of high production costs and limited synthetic methods, providing a new strategy for asymmetric catalysis. The study demonstrates the significance of QUINOL as a key platform molecule for the development of chiral ligands and catalysts in asymmetric catalysis.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Giuseppe Dilauro, Francesco Messa, Fabio Bona, Serena Perrone, Antonio Salomone
Summary: A simple cobalt complex, Co(phen)Cl₂, has been found to be a highly efficient and cost-effective precatalyst for various cross-coupling reactions involving aromatic and aliphatic organoaluminum reagents with aryl, heteroaryl, and alkyl bromides. New C(sp²)-C(sp²) and C(sp²)-C(sp³) bonds can be formed in good to excellent yields and high chemoselectivity under mild reaction conditions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Si-Xuan Zhang, Yan Ding, Jun-Jie Wang, Chuanji Shen, Xiaocong Zhou, Xue-Qiang Chu, Mengtao Ma, Zhi-Liang Shen
Summary: A titanium(IV)-mediated ring-opening/dehydroxylative cross-coupling reaction of diaryl-substituted methanols with a cyclopropanol derivative has been developed. The reactions efficiently provide synthetically useful y,y-diaryl esters in moderate to good yields, which can be applied to functionalizing complex molecules and synthesizing a precursor to Zoloft.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xingwang Deng, Guan Zhou, Xiao Han, Khadim Ullah, Rajavel Srinivasan
Summary: Potassium acyltrifluoroborates (KATs) are opening up new avenues in chemical biology, materials science, and synthetic organic chemistry due to their intriguing reactivities. The chemoselective Pd-catalyzed approaches developed for the late-stage diversification of arenes bearing prefunctionalized KATs feature chemoselective cross-coupling, rapid diversification, functional group tolerance, mild reaction conditions, simple operation, and high yields.
Article
Chemistry, Organic
Hetao Xu, Mingxing Ye, Kai Yang, Qiuling Song
Summary: This study presents a transition-metal-free cross-coupling reaction of isatogens with boronic acids through a 1,4-metalate shift of a boron ate complex. The coupling reaction provides a feasible method to deliver valuable 2,2-disubstituted indolin-3-one derivatives with excellent regioselectivity, operational simplicity, good functional group tolerance, and a broad substrate scope.
Article
Chemistry, Multidisciplinary
Negin Hosseini, Javad Mokhtari, Issa Yavari
Summary: The study presents a copper-catalyzed Sonogashira cross-coupling of phenols using DCID as a new C-O activation agent, successfully matching substituted phenols and phenyl acetylenes under optimized reaction conditions.
