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, Multidisciplinary
Xiaona Yang, Yunfei Guo, Hong'en Tong, Rongfang Liu, Rong Zhou
Summary: In this work, a metal-free acceptorless dehydrogenative cross-coupling reaction for both carbon-heteroatom and carbon-carbon bond formation has been developed. The reaction was achieved through the synergistic catalysis of the organophotocatalyst 4CzIPN and a thiol under blue light irradiation, enabling the coupling of aldehydes with alcohols or two different alcohols with a broad substrate scope and good functional group compatibility. Mechanistic studies revealed the generation and subsequent oxidation of an acyl radical to its cation under photocatalytic conditions.
Review
Chemistry, Multidisciplinary
Jianbin Li, Chia-Yu Huang, Chao-Jun Li
Summary: This review summarises recently developed strategies for achieving C-C cross-couplings between an inert aliphatic C-H bond and another C-H bond through different C(sp3)-H functionalisation tactics.
TRENDS IN CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Tian Tian, Zhiping Li, Chao-Jun Li
Summary: This review explores the development of cross-dehydrogenative coupling (CDC) reactions over the past 20 years and discusses future trends and directions, including the use of alternative energy inputs such as photoredox, mechano, microwave, electrochemical, continuous-flow, and solar quantum dots. These alternative forms of energy are gradually replacing the classical form of thermal energy, inspiring broader applications and innovations in the future.
Article
Chemistry, Organic
Dellamol Sebastian, Patrick H. Willoughby, Mahesh K. Lakshman
Summary: Cross-dehydrogenative coupling reactions were used to alkylate 4(3H)-quinazolinones with ethers and amides, with catalytic n-Bu4NI and t-BuOOH as oxidants. The reactions with amides were the first examples under these conditions. Mechanistic insights were obtained through inter- and intramolecular competitive experiments with protio and deuterio reactants, as well as radical inhibition experiments. Understanding of the relative reactivities of ethers was also achieved through pairwise competitions with 4(3H)-quinazolinone.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Rushil Fernandes, Krishna Mhaske, Reena Balhara, Garima Jindal, Rishikesh Narayan
Summary: Heterobiaryls are important structural motifs in various fields, and the cross-dehydrogenative coupling is actively explored as a greener alternative for their synthesis. A Cu(I)-catalyzed cross-dehydrogenative coupling of indoles and furans using air as oxidant is reported here, showing high selectivity and good yields with broad substrate scope.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Zijuan Yan, Feipeng Liu, Xuchao Wang, Qing Qiang, Yongjie Li, Yao Zhang, Zi-Qiang Rong
Summary: The facile synthetic method presented involves the construction of amides from alcohols and amines catalyzed by Ni/NHC, with advantages such as base metal catalysis, commercially available catalyst, good yields (up to 95%), and substrate generality. The nature of the reaction was revealed through NMR spectroscopy and isolation of intermediates.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Ravichandran Logeswaran, Masilamani Jeganmohan
Summary: This paper reports an oxidative cross-coupling reaction between α,β-unsaturated compounds and unactivated alkenes via cobalt-catalyzed vinylic C-H activation. The reaction was investigated with differently functionalized unsaturated compounds and unactivated olefins, leading to the preparation of valuable amide functionalized butadienes and indenones in good yields. A possible reaction mechanism involving directed olefinic C-H activation through a base-assisted deprotonation pathway is proposed.
Review
Chemistry, Organic
C. M. A. Afsina, Thaipparambil Aneeja, Mohan Neetha, Gopinathan Anilkumar
Summary: Copper-catalyzed organic reactions have attracted widespread attention due to the abundance and affordability of copper, as well as its low toxicity, eco-friendliness, sustainable nature, and versatility as a catalyst. These reactions are primarily used for the synthesis of biologically important nitrogen heterocycles, amines, amides, imines, and alkynes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Wei Wei, Xiaodan Zhao
Summary: The carbon-carbon bond-forming cross-dehydrogenative coupling reaction using organoselenium catalysis involving a high-valent para-methoxyphenyl selenium species has been developed. This method enables the synthesis of alpha,alpha-disubstituted alpha-amino acid derivatives with excellent regioselectivities through vinyl or allylic C-H functionalization. The generality of this method has been demonstrated by the cross-coupling of an alkene with an oxindole and the direct functionalization of electron-rich arenes with azlactones.
Article
Chemistry, Organic
Huan Cao, Chao-Jiu Long, Dan Yang, Zhi Guan, Yan-Hong He
Summary: An unprecedented electrochemical cross-dehydrogenative coupling reaction has been developed for the direct synthesis of alpha-substituted isochromans. This method allows for the direct activation of C(sp3)-H bond adjacent to the O atom of isochroman. It has high atom economy, does not require a chemical oxidant, and is carried out under mild conditions using methanesulfonic acid as both electrolyte and catalyst, making it convenient and environmentally friendly. Gram-scale experiments and synthesis of antitumor active compounds demonstrate the practical applicability of this protocol.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xinyu Chen, Hongqiang Liu, Hui Gao, Pinhua Li, Tao Miao, Hongji Li
Summary: An electrochemical cross-dehydrogenative coupling of indoles with xanthenes has been achieved at room temperature without the need for any catalyst or external oxidant, yielding moderate amounts of indole derivatives. Mechanistic experiments suggest a possible involvement of a radical pathway in this reaction system.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Huan Cao, Chao-Ji u Long, Dan Yang, Zhi Guan, Yan-Hong He
Summary: An unprecedented electrochemical cross-dehydrogenative coupling reaction has been developed for the direct synthesis of α-substituted isochromans by coupling isochroman with unactivated ketones. This method allows for the direct activation of the C(sp(3))-H bond adjacent to the O atom of isochroman and features high atom economy, chemical oxidant-free conditions, and mild reaction conditions. Methanesulfonic acid (MsOH) serves as both electrolyte and catalyst, making the process more convenient and environmentally friendly. Gram-scale experiments and synthesis of antitumor active compounds demonstrate the practical potential of this protocol.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Applied
Ilya N. Egorov, Anindita Mukherjee, Sougata Santra, Dmitry S. Kopchuk, Igor S. Kovalev, Yuanli Liu, Grigory V. Zyryanov, Adinath Majee, Oleg N. Chupakhin, Brindaban C. Ranu
Summary: This review highlights the various applications of cross dehydrogenative coupling reactions under ball milling for the synthesis of useful molecules in a more efficient and convenient manner.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Chang-Xue Gu, Jian-Guo Liu, Wen-Wen Chen, Ming-Hua Xu
Summary: An efficient base-free palladium-catalyzed intramolecular cross dehydrogenative coupling has been developed for the synthesis of diversely substituted coumaronochromones with yields up to 90%.
Article
Chemistry, Organic
Lea Thai-Savard, Morgane Sayes, Josiane Perreault-Dufour, Gang Hong, Lucille A. Wells, Marisa C. Kozlowski, Andre B. Charette
Summary: The borosilylcyclopropanation of styrene derivatives using a (diiodo(trimethylsilyl)methyl)boronic ester carbene precursor is reported, with the key reagent synthesized in a 4-step sequence using inexpensive and commercially available starting materials. This method enables the preparation of novel 1,1,2-tri- and 1,1,2,2-tetrasubstituted borosilylcyclopropanes with excellent yields and diastereoselectivity. The organocatalyzed reaction by eosin Y in the presence of visible light follows a postulated mechanism based on density functional theory calculations, and the versatility of these entities is highlighted through post-functionalization reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jingze Wu, Marisa C. Kozlowski
Summary: A photocatalytic method using an inexpensive heterogeneous titanium dioxide photocatalyst with air and visible light was reported for the oxidative coupling of phenol and alkenylphenol. The Ti-substrate complex was activated under visible light through a ligand to metal charge transfer effect, leading to the formation of a diphenol adduct via a radical cation. The heterogeneous TiO2 catalyst remained stable throughout the reaction and could be easily removed and reused multiple times.
Editorial Material
Chemistry, Multidisciplinary
Marisa C. Kozlowski, Scott J. Miller, Stephane Perreault
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Editorial Material
Chemistry, Inorganic & Nuclear
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, PrashantV. Kamat, Marisa Kozlowski, Geraldine Masson, Scott J. Miller
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Houng Kang, Carilyn Torruellas, Marisa C. Kozlowski
Summary: An asymmetric total synthesis of chaetoglobin A was accomplished by utilizing atroposelective oxidative coupling reaction of a phenol. The stereochemistry of the catalytic oxidative phenolic reaction was found to be opposite to that of the simpler congeners, illustrating the caution needed when extrapolating asymmetric reactions to complex substrates. The optimization of postphenolic coupling steps and difficulties caused by the lability of tertiary acetates in chaetoglobin A were discussed, while the final oxygen to nitrogen exchange proceeded smoothly and the spectroscopic data of the synthetic material matched the natural product.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Miseon Lee, Dennis Sulwey, Madeline E. Rotella, Wan Shin Kim, Xuan Ju, Qi Jiang, Marisa C. Kozlowski, Jaehee Lee
Summary: This study reports the copper catalyzed selective and stereospecific opening of CF3-aziridines. The focus is on the synthesis of α-CF3-β-arylethylamines, which can serve as important intermediates for the synthesis of synthetic analogues and biologically active molecules. Density functional theory calculations provide insights into the active copper species and the role of LiClMgX (X = Cl or I) as a Lewis acid. Furthermore, the computed mechanism explains the high regioselectivity of this transformation.
Editorial Material
Chemistry, Organic
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, Stefanie Dehnen, Prashant V. Kamat, Marisa Kozlowski, Geraldine Masson, Scott J. Miller
Editorial Material
Chemistry, Physical
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, Stefanie Dehnen, Prashant Kamat, Marisa Kozlowski, Geraldine Masson, Scott J. Miller
Editorial Material
Chemistry, Physical
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, Stefanie Dehnen, Prashant V. Kamat, Marisa Kozlowski, Geraldine Masson
ACS ENERGY LETTERS
(2023)
Editorial Material
Chemistry, Multidisciplinary
Tingting Meng, Marisa C. Kozlowski, Tiezheng Jia
TRENDS IN CHEMISTRY
(2023)
Editorial Material
Chemistry, Analytical
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, Stefanie Dehnen, Prashant V. Kamat, Marisa Kozlowski, Geraldine Masson, Scott J. Miller
ACS MEASUREMENT SCIENCE AU
(2023)
Editorial Material
Chemistry, Multidisciplinary
Shelley Minteer, Jingguang Chen, Song Lin, Cathleen Crudden, Stefanie Dehnen, Prashant V. Kamat, Marisa Kozlowski, Geraldine Masson, Scott J. Miller
ACS ORGANIC & INORGANIC AU
(2023)
Article
Chemistry, Organic
Ivan Volchkov, Brent V. Powell, Olga V. Zatolochnaya, Joyce C. Leung, Scott Pennino, Lifen Wu, Nina C. Gonnella, Bangaru Bhaskararao, Marisa C. Kozlowski, Jonathan T. Reeves
Summary: This article reports a practical method for the synthesis of di- and trisubstituted vinyl fluorides through a selective olefination/hydrolysis reaction. The method allows for the production of the desired compounds with high isomeric purity and without the need for tedious chromatography.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Biochemistry & Molecular Biology
Matthew C. Carson, Marisa C. Kozlowski
Summary: Covering the period from 2008 to 2023, this review examines the use of oxidative phenol coupling in the total synthesis of natural products. The review explores catalytic and electrochemical methods, comparing them to stoichiometric and enzymatic systems in terms of practicality, atom economy, and other factors. It also discusses the synthesis of natural products through C-C and C-O oxidative phenol couplings, as well as alkenyl phenol couplings. Additionally, the review surveys the catalytic oxidative coupling of phenols and other related species, such as carbazoles, indoles, and aryl ethers. Future research directions in this field are also assessed.
NATURAL PRODUCT REPORTS
(2023)
