Article
Multidisciplinary Sciences
Dingyi Wang, Mingjie Li, Chengdong Shuang, Yong Liang, Yue Zhao, Minyan Wang, Zhuangzhi Shi
Summary: The authors report a method that appends arenes to arylphosphines via rhodium-catalyzed P(III)-directed ortho C-H activation, enabling one-fold, two-fold, and three-fold direct arylation of these compounds. This method provides a solution to the challenges associated with the modular preparation of biaryl monophosphines.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Haoqiang Zhao, Jianbin Xu, Xin Xu, Yixiao Pan, Zexin Yu, Lijin Xu, Qinghua Fan, Patrick J. Walsh
Summary: The method employs inexpensive, readily available, and safe aryl carboxylic acids with a pyridine directing group to achieve C6-selective C-H arylation, allowing for a wide range of substituted 2-pyridones and affording products in yields of 41-91%.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
Liming Zhang, Ru Zhao, Chunhui Liu, Zhaoyang Li, Jun-Long Niu, Hao-Ran Yang, Lijun Gao, Shuang-Liang Liu, Liming Zhou
Summary: The Rh(III)-catalyzed ortho alkylation of N-pyridylcarbazoles with nitroalkenes has been developed for the synthesis of a wide range of 2-(2nitroalkyl)carbazoles. Aromatic and aliphatic nitroalkenes both successfully participated in this alkylation reaction. The protocol also worked well with an indoline based substrate. Derivatization of the representative nitroalkane product was described.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Bartlomiej Sadowski, Binbin Yuan, Zhipeng Lin, Lutz Ackermann
Summary: In this study, electrocatalytic peri C-H alkenylation of 1-naphthols was achieved using rhodium(III) catalysis under constant current electrolysis conditions. This strategy offers a wide scope, good functional group tolerance, and high site- and stereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yi-Ming Wei, Xiao-Di Ma, Meng-Fei Wang, Xin-Fang Duan
Summary: Fe-catalyzed difunctionalization of aryl titanates through double C-H activation has been developed. Aryl titanates are arylated via ortho C-H activation, followed by ipso electrophilic trapping of the C-Ti bond. The ortho C-H arylation is promoted by a 1,2-Fe/Ti heterobimetallic arylene intermediate and involves another ortho C-H activation directed by benzamides, esters, and nitriles.
Article
Chemistry, Applied
Hisanori Nambu, Ryoya Amano, Takafumi Tamura, Takayuki Yakura
Summary: This study describes the dirhodium(II)-catalyzed intramolecular insertion of aryldiazoacetates into unactivated primary C-H bonds. The reaction shows high selectivity and provides a direct route to 2-unsubstituted indane-1-carboxylates and specific isomers with ortho-substituted groups. Furthermore, a chemoselective C-H insertion reaction of aryldiazoacetate with a 1-oxyethyl substituent is achieved using a specific protecting group.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Prakash Basnet, Gang Hong, Charles E. Hendrick, Marisa C. Kozlowski
Summary: A copper-catalyzed carbochlorination reaction of alkenes with aryl malononitriles and chloride was demonstrated, yielding products that can be further converted into biologically important gamma-lactones. Mechanistic studies indicate the formation of a secondary carbon radical, which reacts with a chloride source to give the desired products. The reaction works well with both activated and unactivated alkenes, providing moderate to excellent yields.
Article
Chemistry, Applied
Zheng-Qiang Liu, Jing Tao, Xin Zhuang, Chuan-Ming Hong, Zhen Luo, Yu-Fei Wu, Qing-Hua Li, Tang-Lin Liu
Summary: The rhodium(III)-catalyzed aryl borrowing amination allows for the reaction between various diaryl methanols with sulfonamides, showing good functional group tolerance and mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Shrikant M. Khake, Naoto Chatani
Summary: The Rh(III)-catalyzed C-H oxidative alkylation of aniline derivatives with readily available secondary allyl alcohols is described. The reaction exhibited tolerance towards various functional groups. Different oxidants are required depending on the structure of the allyl alcohol. Mechanistic experiments revealed insights into the catalyst regeneration step.
Article
Chemistry, Organic
Gao Huang, Jin-Tao Yu, Changduo Pan
Summary: A rhodium-catalyzed C-H activation/annulation of N-aryl-pyrazolidinones with vinylene carbonate was developed, leading to the successful construction of non-substituted 5,6-pyrazolo[1,2-a]cinnoline derivatives. This method provides an efficient and selective approach to synthesizing these derivatives, which are challenging to obtain using other procedures. Importantly, the protocol does not require external oxidants and generates water and carbon dioxide as clean by-products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhensheng You, Yusuke Masuda, Tomohiro Iwai, Kosuke Higashida, Masaya Sawamura
Summary: A Ni-catalyzed cross-coupling reaction between aryl fluorides and dialkyl phosphonates has been reported. The reaction converts various aryl fluorides into the corresponding aryl phosphonates, even with electron-donating substituents on the aromatic ring. The mechanism studies suggest that the Ni-K+ cooperative action plays a crucial role in facilitating the turnover-limiting step.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhensheng You, Yusuke Masuda, Tomohiro Iwai, Kosuke Higashida, Masaya Sawamura
Summary: A new catalytic system has been developed for the cross-coupling reaction between aryl fluorides and dialkyl phosphonates. The reaction shows excellent functional group tolerance and the reaction mechanism has been elucidated through experimental and computational studies.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Boya Feng, Guodong Zhang, Xu Feng, Yu Chen
Summary: A palladium-catalyzed decarbonylative methylation of aryl carboxylic acids using trimethylboroxine as the methylating reagent is described. The Pd(OAc)(2)/XantPhos system is compatible with a wide range of carboxylic acids and derivatives, including aroyl chloride/fluoride. The successful methylation of bioactive molecules and examples of orthogonal cross-couplings demonstrate the practicality of this method.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Takanobu Saito, Joaquim Caner, Naoyuki Toriumi, Nobuharu Iwasawa
Summary: A novel method for the meta-selective C-H carboxylation of 1,1-diarylethylene derivatives using a rhodium catalyst and a stoichiometric reductant has been achieved. The introduction of a carboxyl group to the aryl ring at the meta-position was enabled with high selectivity. Both experimental and computational mechanistic studies indicate that a specific rhodium migration process plays a key role in this unusual aryl-to-aryl 1,2-rhodium shift.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Guoshuai Li, Yifei Yan, Pengfei Zhang, Xiaohua Xu, Zhong Jin
Summary: A new palladium-catalyzed meta-selective C-H olefination of aromatic carbonyl compounds was achieved by utilizing noncovalent hydrogen-bonding interaction directed by engineered N,N'-substituted ureas, demonstrating site-selective control without the need for prior stoichiometric installation and removal of directing groups.
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)