Review
Chemistry, Organic
Aanchal Batra, Pushpinder Singh, Kamal Nain Singh
Summary: Developing greener and atom economical methods for carbon-heteroatom bond formation is crucial in synthetic organic chemistry. Metal-free cross-dehydrogenative coupling (CDC) is an attractive approach due to its ease and environmental friendliness, and this review focuses on recent developments in this area.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Weiqi Liu, Xinghao Jin, Dawei Ma
Summary: The requirement of higher reaction temperatures for SNAr reaction between thiols and less reactive electron-poor aryl halides has led to the development of metal- and photo-catalyzed methods. In this study, the SNAr reaction between thiols and most electron-poor aryl halides was found to occur at RT-60°C using K2CO3 and DMAc. Additionally, two oxalic diamide ligands were identified to enable Cu-catalyzed coupling reactions with low catalytic loadings for unreactive (hetero)aryl halides, offering a promising approach for preparing (hetero)aryl thioethers.
Article
Chemistry, Multidisciplinary
Jian Wang, Changqing Tu, Mei-Lin Feng, Nan Li
Summary: A metal-free reaction system utilizing TEMPO and PhI(OAc)(2) has been developed for the oxidative C-N coupling of benzoxazoles with NH-sulfoximines, resulting in moderate to high yields of corresponding 2-iminoazoles under ambient atmosphere without any metal catalyst at room temperature.
Review
Chemistry, Organic
Kifah S. M. Salih
Summary: This review article highlights the recent development and sustainable achievement of copper- and nickel-catalyzed cross-coupling reactions, especially under microwave irradiation conditions. The published cross-coupling protocols in the past decade were critically reviewed, and the proposed reaction mechanisms involving metal complexes in different oxidation states were discussed.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Long Liu, Yuanyuan Tang, Kunyu Wang, Tianzeng Huang, Tieqiao Chen
Summary: A facile and general method for constructing carbon-heteroatom bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled the coupling of a wide range of substituted benzyl ammonium salts with heteroatom nucleophiles. Good functional group tolerance was demonstrated, and scale-up reactions and one-pot syntheses were successfully performed.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Applied
Zhongyi Zeng, Abigail Feceu, Nardana Sivendran, Lukas J. Goossen
Summary: Carboxylic acids and their derivatives play a key role in decarboxylative couplings for constructing C-C and C-heteroatom bonds, offering a complementary bond disconnection to traditional cross-coupling methods. By undergoing decarboxylation and reacting with other heteroatom electrophiles and nucleophiles, these compounds replace carboxylate groups with valuable and prevalent heteroatom functionalities.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Jian Luo, Michael. T. T. Davenport, Chad Callister, Shelley. D. D. Minteer, Daniel. H. H. Ess, T. Leo Liu
Summary: In this study, the mechanism of Ni-catalyzed electrochemical aryl amination reactions was investigated through experiments and calculations. The results revealed that the coordination of an amine to the Ni-II catalyst, followed by the generation of a stable Ni-II aryl amido intermediate and reductive elimination, were key steps in the reaction. The findings provide new insights into the mechanism of this reaction and offer guidance for the development of other Ni-catalyzed electrosynthetic reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Shaofeng Wu, Furong Geng, Jianyu Dong, Long Liu, Yongbo Zhou
Summary: A metal-free and highly general synthesis of benzoxazoles from abundant phenols and amines has been developed using TEMPO-controlled phenol functionalization. This method offers advantages in terms of generality, selectivity, efficiency, and atom-and-step economies over traditional methods.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Biprajit Paul, Hrishikesh Paul, Indranil Chatterjee
Summary: This review highlights the development of photoredox-mediated desulfonylation reactions since 2000, which have emerged as a powerful strategy for C-C and C-X bond formation. The mild reaction conditions, wide functional group tolerance, and excellent synthetic efficacy make these reactions highly attractive in synthetic organic, bio, and material chemistry.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Xinxin Qiao, Yong-De Zhao, Mingru Rao, Zhan-Wei Bu, Guangwu Zhang, Heng-Ying Xiong
Summary: An unexpected cleavage of the C-sp3-CF3 bond of CF3-hydrobenzoxazoles has been discovered, leading to the synthesis of a range of 2-aryl benzoxazoles under metal-free and redox-neutral conditions. The reaction demonstrates broad substrate scope and good compatibility of functional groups, offering an alternative, facile, and sustainable route to access important 2-aryl benzoxazole motifs.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Chen Zhu, Huifeng Yue, Jiaqi Jia, Magnus Rueping
Summary: The formation of C-heteroatom bonds through recent advances in homo- and heterogeneous Ni-catalyzed reactions under mild conditions is attractive due to sustainability and practicability. The generation of Ni-III and excited Ni-II intermediates enables mild cross-couplings, leading to the development of various catalytic systems involving photoredox and nickel dual catalysis, photoexcited nickel catalysis, electro and nickel dual catalysis, and heterogeneous photoredox and nickel dual catalysis using different materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Tian-Yu Peng, Feng-Lian Zhang, Yi-Feng Wang
Summary: This article summarizes the research progress on boron-centered radicals over the past few decades, with a focus on NHC-boryl radical mediated radical borylation reactions and selective activation of inert carbon-heteroatom bonds. The study demonstrates the potential for developing more powerful and valuable synthetic applications of LBRs and the promising opportunities for discovering new reactions.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Organic
Peng Yang, Xia Wang, Liang Wang, Jiahua He, Qian Zhang, Dong Li
Summary: A novel metal-free C-N bond formation method was developed through oxidative cross-dehydrogenative coupling between iodoarenes and acylanilides, mediated by mCPBA. The reaction exhibited high para-selectivity with retention of the iodine atom, enabling further transformations. This method is characterized by substrate availability, easy operation, and atom economy, providing a simple and efficient route for the preparation of functionalized N-aryl amides.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Physical
Hang Luo, Yunhui Feng, Luqing Lin
Summary: This review focuses on the discussion of variant nickel(II) complexes as precatalysts for forging diverse carbon-heteroatom bonds under visible-light irradiation in the absence of exogenous photocatalysts. Summary of photoactive nickel catalysis aims to promote the development of cheap, abundant metals catalyzed carbon-heteroatom couplings for efficient preparation of highly valuable chemicals.
Article
Chemistry, Organic
Andrew J. Greenlee, Heyu Chen, Chloe I. Wendell, Jeffrey S. Moore
Summary: This study demonstrates the preparation of a three-rung molecular ladder 8 in one pot via tandem reactions, and investigates its assembly and disassembly, showing that catalyst VI is effective but susceptible to deactivation by hydrolysis and ligand exchange.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Trimurtulu Kotipalli, Veerababurao Kavala, Donala Janreddy, Vijayalakshmi Bandi, Chun-Wei Kuo, Ching-Fa Yao
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Sachin S. Ichake, Ashok Konala, Veerababurao Kavala, Chun-Wei Kuo, Ching-Fa Yao
Article
Chemistry, Multidisciplinary
Bharath Kumar Villuri, Trimurtulu Kotipalli, Veerababurao Kavala, Sachin S. Ichake, Vijayalakshmi Bandi, Chun-Wei Kuo, Ching-Fa Yao
Article
Chemistry, Multidisciplinary
Chia-Yu Huang, Chun-Wei Kuo, Ashok Konala, Tang-Hao Yang, Lyu Lin, Yu-Wen Chen, Veerababurao Kavala, Ching-Fa Yao
Article
Chemistry, Organic
Sachin S. Ichake, R. R. Rajawinslin, Veerababurao Kavala, Bharath Kumar Villuri, Huei-Ting Yang, Chun-Wei Kuo, Ching-Fa Yao
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Chia-Yu Huang, Veerababurao Kavala, Chun-Wei Kuo, Ashok Konala, Tang-Hao Yang, Ching-Fa Yao
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Veerababurao Kavala, Zonghan Yang, Ashok Konala, Chia-Yu Huang, Chun-Wei Kuo, Ching-Fa Yao
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Vijayalakshmi Bandi, Veerababurao Kavala, Che-Hao Hsu, Ashok Konala, Bharath Kumar Villuri, Trimurtulu Kotipalli, Chun-Wei Kuo, Ching-Fa Yao
Article
Chemistry, Organic
Veerababurao Kavala, Zonghan Yang, Ashok Konala, Tang-Hao Yang, Chun-Wei Kuo, Jian-Yao Ruan, Ching-Fa Yao
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Bharath Kumar Villuri, Sachin S. Ichake, Sabbasani Rajasekhara Reddy, Veerababurao Kavala, Vijayalakshmi Bandi, Chun-Wei Kuo, Ching-Fa Yao
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Vijayalakshmi Bandi, Veerababurao Kavala, Ashok Konala, Che-Hao Hsu, Bharath Kumar Villuri, Sabbasani Rajasekhara Reddy, LiChun Lin, Ching-Fa Yao
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Sachin S. Ichake, Bharath Kumar Villuri, Sabbasani Rajasekhara Reddy, Veerababurao Kavala, Ching-Fa Yao
Article
Chemistry, Organic
Sundaramoorthi Sarathkumar, Veerababurao Kavala, Ching-Fa Yao
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Applied
Bharath Kumar Villuri, Ashok Konala, Veerababurao Kavala, Trimurtulu Kotipalli, Chun-Wei Kuo, Ching-Fa Yao
ADVANCED SYNTHESIS & CATALYSIS
(2017)
Article
Chemistry, Multidisciplinary
Tang-Hao Yang, Chun-Wei Kuo, Veerababurao Kavala, Ashok Konala, Chia-Yu Huang, Ching-Fa Yao
CHEMICAL COMMUNICATIONS
(2017)