Article
Chemistry, Organic
Fang Wang, Jiaming Chen, Xiaoqi Jia, Dailin Zhuang, Zhenyang Wan, Lifang Ma, Ziyuan Li
Summary: A remote directing group-enabled radical relay strategy for benzylic direct C(sp3)-H alkoxylation with alcohols at room temperature is developed, which achieves satisfactory site-selectivity, chemoselectivity, and reaction scope under simple and mild conditions without the need for ligands or additives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Jinwei Sun, Yongze Zhou, Rui Gu, Xin Li, Ao Liu, Xuan Zhang
Summary: Here, the authors report a nickel-catalyzed method for the silylative alkylation of activated olefins using chlorosilanes and alkyl bromides. This approach enables the efficient synthesis of alkylsilanes with diverse structures and demonstrates good functional group tolerance. The method can also be applied for the functionalization of bioactive molecules.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Liang Hu, Guangrong Meng, Jin-Quan Yu
Summary: This study reports the first Pd(II)-catalyzed intermolecular fi-methylene C(sp3)-H arylation of free aliphatic acids using bidentate pyridine-pyridone ligands. The bite angle of the ligand plays a key role in promoting fi-methylene C-H activation of free carboxylic acid. This transformation provides a disconnection for alkylation of arenes with simple aliphatic acids.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Daniel M. Lux, Vivek Aryal, Doleshwar Niroula, Ramesh Giri
Summary: We report a Ni-catalyzed regioselective dialkylation reaction of alkenylarenes with α-halocarbonyls and alkylzinc reagents. The reaction generates α-arylated alkanecarbonyl compounds with the formation of two new C(sp(3))-C(sp(3)) bonds at the vicinal carbons of alkenes. This reaction is suitable for primary, secondary, and tertiary α-halocarboxylic esters, amides, and ketones, in combination with primary and secondary alkylzinc reagents as the sources of two C(sp(3)) carbons for the dialkylation of terminal and cyclic internal alkenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Xi Chen, Zhe Zhang, Wei-Yu Shi, Ya-Nan Ding, Yu-Yong Luan, Yan-Chong Huang, Qiang Wang, Xue-Yuan Liu, Yong-Min Liang
Summary: We report a redox-neutral, visible-light-mediated difluoroalkylation of unactivated C(sp(3))-H bonds in amides via nitrogen-centered radicals triggered intramolecular hydrogen atom transfer. All types of gamma-C(sp(3))-H bonds exhibited excellent reactivity. This methodology provides a facile route for regioselective introduction of alpha,alpha-difluoroketonefragments into organic molecules, which can be easily converted to structurally diverse difluoro-containing molecules with broad potential applications in medicinal chemistry and chemical biology.
Article
Chemistry, Organic
Sumit, Devesh Chandra, Ankita Thakur, Ankit Kumar Dhiman, Upendra Sharma
Summary: In this study, a highly regioselective trifluoromethylthiolation of the unactivated C(sp(3))-H bond of 8-methylquinolines catalyzed by Rh(III) was explored, with good yields and high regioselectivity. The reaction conditions are also applicable for late-stage functionalization of natural molecules santonin and caffeine-substituted 8-methylquinoline.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Zhifan Wang, Beiqi Yang, Qi Yang, Yuanhua Wang
Summary: In this study, a method for the successful synthesis of 1,3-diamines through the simultaneous and direct amination of multiple inert Csp(3)-H bonds was developed using a radical sequential reaction mediated by a dirhodium(ii) catalyst. The reaction involved the interaction of cumene derivatives with N-fluorobenzenesulfonimide (NFSI) and underwent an iterative radical polar crossover and desaturation activation procedure to activate three adjacent C-H bonds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Jia-Lin Tu, Ao-Men Hu, Lin Guo, Wujiong Xia
Summary: In this study, undirected iron-catalyzed C(sp3)-H borylation, thiolation, and sulfinylation reactions were developed using the photoinduced ligand-to-metal charge transfer (LMCT) process. These reactions showed broad substrate scope and unconventional regioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Applied
Hui-Min Jiang, Qing Sun, Jin-Peng Jiang, Jing-Hao Qin, Xuan-Hui Ouyang, Ren-Jie Song
Summary: We have described a method for the dicarbofunctionalization of alkenes, which allows for the introduction of alkyl and electron-rich aryl groups across the C=C bond of styrenes. This is achieved under copper catalyst and oxidative conditions, resulting in the construction of C(sp(3))-C(sp(2))/C(sp(3))-C(sp(3)) bonds via dual C-H functionalization. The method enables the synthesis of 1,1-diarylalkanes, which are important scaffolds found in natural products and drug molecules, by grafting electron-rich aromatics such as indoles, pyrroles, and trisubstituted aromatics.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Jian-Xin Zhang, Wei Shu
Summary: A Ni-catalyzed reductive 1,2-dialkylation reaction of unactivated aliphatic alkenes using two different alkyl bromides has been developed. The reaction proceeds smoothly under mild conditions, allowing the installation of two C-sp3-C-sp3 bonds onto directed aliphatic alkenes with excellent chemo- and regioselectivity and good functional group tolerance.
Article
Chemistry, Organic
Javeed Ahmad Tali, Ravi Shankar
Summary: Here, we report an unprecedented protocol using ruthenium-catalyzed annulation for the synthesis of 6H-chromeno[4 ',3 ':4,5]imidazo[1,2-a]pyridin-6-one, and a new method for intramolecular chelation-assisted C-H activation to produce functionalized 2-(3-formylimidazo[1,2-a]pyridin-2-yl)phenyl acetate. Furthermore, a one-pot approach using ruthenium catalysis and formic acid has been developed for the gram-scale synthesis of bis(2-phenylimidazo[1,2-a]pyridin-3yl)methane (BIP) and the late-stage functionalization of zolimidine, a marketed drug, with good yield.
Article
Chemistry, Organic
Shogo Nakamura, Soshi Nishino, Koji Hirano
Summary: A copper-catalyzed regioselective hydroamination method was developed to synthesize alpha-aminophosphonates from alpha,beta-unsaturated phosphonates, which are of interest in medicinal chemistry. The use of an umpolung, electrophilic amination strategy with a hydroxylamine derivative is key to achieving the desired regioselectivity, as compared to the conventional nucleophilic hydroamination conditions with the parent amine. The article also discusses the asymmetric synthesis using a chiral bisphosphine ligand and its application in a related silylamination reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Wen-Hui Sun, Jian-Yu Zou, Xiao-Jing Xu, Jin-Lin Wang, Mei-Ling Liu, Xue-Yuan Liu
Summary: In this report, a mild reaction condition was presented for the difunctionalization of alkenes, enabling the construction of complex compounds. The mechanism involves the addition of tertiary alkyl radicals to alkenes followed by nucleophilic addition with aldehydes. The catalyst system shows good functional group compatibility, regioselectivity, and the ability to construct two tertiary carbon centers simultaneously.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Dao-Ming Wang, Li-Qin She, Hao Yuan, Yichen Wu, Yong Tang, Peng Wang
Summary: We reported a Ni-catalyzed hydroxylarylation reaction of unactivated alkenes using molecular oxygen as the oxidant and hydroxyl source. This reaction showed high efficiency, excellent regioselectivity, mild reaction conditions, broad substrate scope, and remarkable heterocycle compatibility, providing a wide range of valuable compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xiaoxu Yang, Chunchen Yuan, Shaozhong Ge
Summary: The development of protocols for stereodivergent synthesis of multi-substituted alkenylboronates simplifies and unifies the synthesis of Z and E stereoisomers of multi-substituted alkenes. Although various efforts have been made to achieve stereoselective approaches to access Z or E alkenylboronates, catalyst-controlled stereodivergence in their synthesis is still rare. This study demonstrates that stereodivergence can be achieved for nickel-catalyzed hydroboration of internal allenes, enabling the convenient synthesis of both stereoisomers of trisubstituted alkenylboronates.
Article
Chemistry, Organic
Sophia J. Bailey, Rishi R. Sapkota, Alexandra E. Golliher, Barry Dungan, Marat Talipov, F. Omar Holguin, William A. Maio
Article
Chemistry, Multidisciplinary
Rishi R. Sapkota, Jacqueline M. Jarvis, Tanner M. Schaub, Marat R. Talipov, Jeffrey B. Arterburn
Article
Environmental Sciences
Lu Lin, Wenbin Jiang, Mikhael Bechelany, Maryline Nasr, Jacqueline Jarvis, Tanner Schaub, Rishi R. Sapkota, Philippe Miele, Huiyao Wang, Pei Xu
Article
Chemistry, Multidisciplinary
Doleshwar Niroula, Rishi R. Sapkota, Roshan K. Dhungana, Bijay Shrestha, Ramesh Giri
ISRAEL JOURNAL OF CHEMISTRY
(2020)
Article
Chemistry, Organic
Ryan A. S. Pike, Rishi R. Sapkota, Bijay Shrestha, Roshan K. Dhungana, K. C. Shekhar, Diane A. Dickie, Ramesh Giri
Article
Chemistry, Multidisciplinary
Roshan K. Dhungana, Rishi R. Sapkota, Laura M. Wickham, Doleshwar Niroula, Bijay Shrestha, Ramesh Giri
Summary: In this study, a Ni-catalyzed regioselective arybenzylation of alkenylarenes with benzyl halides and arylzinc reagents was reported. The reaction yields differently substituted 1,1,3-triarylpropyl structures reminiscent of oligoresveratrol natural products. Kinetic studies show that the reaction proceeds via a rate-limiting single-electron-transfer process and is autocatalyzed by in-situ-generated ZnX2, leading to a three-fold increase in reaction rate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Roshan K. Dhungana, Vivek Aryal, Doleshwar Niroula, Rishi R. Sapkota, Margaret G. Lakomy, Ramesh Giri
Summary: A nickel-catalyzed reaction was developed for difunctionalizing unactivated gamma,delta-alkenes in ketones with alkenyl triflates and arylboronic esters. The reaction, facilitated by specific ligands and catalysts, demonstrated compatibility with various types of ketones and arylboronate esters, requiring carbonyl coordination for its progress.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Correction
Chemistry, Multidisciplinary
Roshan K. Dhungana, Rishi R. Sapkota, Laura M. Wickham, Doleshwar Niroula, Ramesh Giri
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
Roshan K. Dhungana, Rishi R. Sapkota, Doleshwar Niroula, Ramesh Giri
Meeting Abstract
Chemistry, Multidisciplinary
Rishi Sapkota, Jacqueline M. Jarvis, Neil Paz, Tanner Schaub, Jeffrey Arterburn
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Meeting Abstract
Chemistry, Multidisciplinary
Rishi Sapkota, Miguel Garcia, Kodanda Dandamudi, Tanner Schaub, Jeffrey Arterburn
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2015)