Article
Chemistry, Physical
Qing-Peng Liu, Xiaoyu Chen, Ning Yu, Yu-Lin Li, Kui-Cheng He, Wei-Hao Zheng, Yu-Qiang Zhou, Kun Jiang, Limin Yang, Ye Wei
Summary: In this work, a relay C-H functionalization protocol using iron catalysis was described, which enables the synthesis of various pyridines and pyridones. The reaction involves the functionalization of three C-H bonds and the generation of three chemical bonds and two rings in one step. The reaction mechanism was investigated through control experiments and kinetic isotope effect experiments.
Article
Chemistry, Multidisciplinary
Kristina Plevova, Peter Kisszekelyi, Denisa Vargova, Samuel Andrejcak, Viktor Toth, LukaS Fertal, Erik Rakovsky, Juraj Filo, Radovan Sebesta
Summary: This study demonstrates the diastereoselective double C-H heteroarylation of chiral ferrocenes using Pd-complexes with chiral mono-protected amino acids, resulting in a variety of functionalized compounds. The absolute configurations of CH-activation products were confirmed using X-ray crystallographic analysis and CD spectroscopy, while insights into the reaction mechanism and stereoinduction were provided by F-19 NMR kinetic study and DFT calculations.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Grazia Bencivenni, Diana Salazar Illera, Maria Moccia, K. N. Houk, Joseph A. Izzo, Johanna Novacek, Paolo Grieco, Mathew J. Vetticatt, Mario Waser, Mauro F. A. Adamo
Summary: Through H-1 NMR titration experiments, it was found that chiral ammonium salts interact with substrates through specific C-H positions, providing a new rationale for rationalizing the enantioselectivity in chiral phase-transfer catalysis.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Chengqiang Cao, Yi Yang, Xin Li, Yunxia Liu, Hui Liu, Zengdian Zhao, Lei Chen
Summary: The reaction, catalyzed by palladium, efficiently constructs two new bonds with high yields, while the alkene group is easily functionalized, leading to the formation of products with a unique structure that is difficult to synthesize.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Tomer M. Faraggi, Caroline Rouget-Virbel, Juan A. Rincon, Mario Barberis, Carlos Mateos, Susana Garcia-Cerrada, Javier Agejas, Oscar de Frutos, David W. C. MacMillan
Summary: The conversion of serine to optically pure unnatural amino acids can be achieved through a two-step process utilizing a photocatalytic cross-electrophile coupling. This method produces artificial analogues of phenylalanine, tryptophan, and histidine, and is tolerant of a broad range of functionalities. It can also be leveraged for the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Organic
Giorgos Yatzoglou, Matthew T. Zambri, Shrey P. Desai, Mark S. Taylor
Summary: The efficient dehydrative couplings of allylic alcohols and tautomerizable heterocycles were achieved by using a boronic acid co-catalyst along with a palladium complex. This protocol has been successfully applied to achieve N-allylations of various heterocycles.
Article
Chemistry, Multidisciplinary
Andrew Whyte, Jonathan Bajohr, Ramon Arora, Alexa Torelli, Mark Lautens
Summary: An enantioselective consecutive cyclization/coupling process catalyzed by palladium was reported in this study. The stereoinduction was achieved through an enantioselective carbopalladation, leading to the generation of an intermediate that promotes a nucleopalladation step. This dual cyclization sequence was compatible with various nucleophiles and aryl iodides, producing numerous bisheterocycles in good yields and high regio- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Steffen Gressies, Lars Süsse, Tyler Casselman, Brian M. Stoltz
Summary: Here, we report a multistep one-pot reaction that converts substituted pyridines into N-protected tetrahydropyridines with excellent enantioselectivity (up to 97% ee). By using an iridium-(I)-catalyzed dearomative 1,2-hydrosilylation of pyridines, N-silyl enamines serve as a new type of nucleophile in a subsequent palladium-catalyzed asymmetric allylic alkylation. This telescoped process overcomes the inherent nucleophilic selectivity of pyridines to synthesize enantioenriched, C-3-substituted tetrahydropyridine products that are otherwise challenging to access.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Maofu Pang, Le-Le Shi, Yufang Xie, Tianyi Geng, Lan Liu, Rong-Zhen Liao, Chen-Ho Tung, Wenguang Wang
Summary: Selective transfer hydrogenation of pyridines to N-H 1,4-dihydropyridines has been achieved by cobalt-amido cooperative catalysis using H3NmiddotBH3 as a dihydrogen source. The reactions exhibit high chemo- and regioselectivity under mild conditions, providing a practical method to regenerate Hantzsch analogues after H2 delivery.
Article
Chemistry, Multidisciplinary
Cang Cheng, Xiang Zuo, Dongdong Tu, Bin Wan, Yanghui Zhang
Summary: A method for the synthesis of enantiopure eight-membered nitrogen heterocycles has been developed through diastereoselective cross-coupling of 2-iodobiphenyls with 2-bromobenzylamines. The products provide a new type of chiral scaffold with easy modification and high configurative stability, which could be used in asymmetric synthesis. Palladacycles formed via the C-H activation of 2-iodobiphenyls act as the intermediates, offering a new strategy for synthesizing medium-sized ring compounds.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Organic
Helene Pellissier
Summary: This review provides an update on the field of asymmetric cascade palladium catalysis for the synthesis of chiral heterocycles since 2019. It demonstrates the use of diverse chiral palladium catalysts to promote unprecedented asymmetric domino reactions, leading to the direct synthesis of complex and densely functionalized chiral heterocyclic molecules.
CURRENT ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Yong Shang, Chenggui Wu, Qianwen Gao, Chang Liu, Lisha Li, Xinping Zhang, Hong-Gang Cheng, Shanshan Liu, Qianghui Zhou
Summary: The derivatives of heterocycles 2-pyridone and uracil are important pharmacophores in medicinal chemistry, and there is an urgent need for diverse synthesis of such derivatives. This study demonstrates that palladium/norbornene cooperative catalysis enables dual-functionalization of iodinated 2-pyridones and uracils.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Jun-Jie Tian, Rui-Rui Li, Gui-Xiu Tian, Xiao-Chen Wang
Summary: Here, we describe a new method for enantioselective C-H allylation of pyridines at C3 using a tandem borane and palladium catalysis. This method involves borane-catalyzed pyridine hydroboration, palladium-catalyzed enantioselective allylation of the resulting dihydropyridines with allylic esters, and air oxidation to afford the products. This method allows for the introduction of an allylic group at C3 with excellent regio- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Guangyu Cui, Xiangqing Feng, Haifeng Du
Summary: The asymmetric hydrogenation of N-heteroarenes provides an efficient method for the synthesis of optically active cyclic secondary amines. In this paper, an asymmetric hydrogenation of phenanthridines using a chiral monoene-derived borane was described. Various optically active dihydrophenanthridines were obtained in high yields with up to 93% ee. The steric hindrance of phenanthridines played a crucial role in both reactivity and enantioselectivity.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Applied
Manon Genet, Abdelilah Takfaoui, Jerome Marrot, Christine Greck, Xavier Moreau
Summary: A series of enantioenriched 4,5,6,7-tetrahydrofuro[2,3-b]pyridines were synthesized using a cycloisomerization/cycloaddition strategy, with yields ranging from 27% to 90% and high levels of stereoselectivity. Sequential relay catalysis with a gold complex and a diphenylprolinol silyl ether was successfully applied to a combination of diversely functionalized substrates.
ADVANCED SYNTHESIS & CATALYSIS
(2021)