Article
Chemistry, Applied
Seoyoung Lee, Juyeong Kim, Kyungjun Kang, Ansoo Lee, Hyunwoo Kim
Summary: In this study, we developed a ligand-controlled palladium-catalyzed allylic substitution approach that selectively achieves [1+1] and [1+2] allylic aminations between allylic diols and diamines. By combining this approach with sequential acetylation and allylic amination, tetraazamacrocycles with ring sizes ranging from 16 to 38 were successfully synthesized. These findings demonstrate the potential of a sequential allylation strategy for synthesizing complex molecules with broad applications in the fields of chemistry, pharmaceuticals, and medicine.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Organic
Mohini Shrestha, Xianqing Wu, Wenyi Huang, Jingping Qu, Yifeng Chen
Summary: This review article summarizes the development of carbamoyl chlorides as synthons for various amide-containing molecules and heterocycles in transition metal-catalyzed reactions. It highlights the advancements and applications of carbamoyl chlorides in organic framework synthesis, as well as briefly discusses the chemical behavior of their structural analogs.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Nardana Sivendran, Nico Pirkl, Zhiyong Hu, Angelino Doppiu, Lukas J. Goossen
Summary: Halogen-bridged methylnaphthyl (MeNAP) palladium dimers, presented as versatile Pd precursors, demonstrate excellent catalytic performance by in situ conversion into well-defined monoligated complexes. They show benchmark activities in challenging reactions, enable record-setting yields, and can achieve previously elusive cross-couplings.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Weixu Lu, Xiaoqiang Yu, Ming Bao
Summary: In this paper, a group of copper-based ternary deep eutectic solvents (Cu-DESs) were synthesized and applied in Glaser-type homo- and cross-coupling of terminal alkynes. These reactions occurred under exogenous-ligand-free, base-free, and additive-free conditions, providing satisfactory to excellent yields (up to 99%) under mild conditions. The Cu-DESs can be recycled eight times, with water being the only by-product, complying fully with the principles of green chemistry.
Article
Chemistry, Inorganic & Nuclear
Lingyu Kong, Yajie Chou, Muriel Albalat, Marion Jean, Nicolas Vanthuyne, Stephane Humbel, Paola Nava, Herve Clavier
Summary: The concept of atropisomeric N-heterocyclic carbene (NHC)-metal complexes with C-2-symmetry was extended to palladium-based complexes. Through a comprehensive study of NHC precursors and screening of various NHC ligands, the formation of meso complexes was successfully circumvented. Eight atropisomeric NHC-palladium complexes were prepared and obtained with high enantiopurities through efficient chiral HPLC resolution. These complexes demonstrated good activity in the intramolecular alpha-arylation of amides, leading to the isolation of cyclic products with excellent enantioselectivities (up to 98% ee).
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Organic
Nandarapu Kumarswamyreddy, Samydurai Jayakumar, Venkitasamy Kesavan
Summary: This study demonstrates the successful asymmetric allylic alkylation reaction catalyzed by a tartrate derived bi(oxazoline) ligand with palladium (II) species, achieving highly valuable 3-allyl-3-amino-2-oxindoles. The synthesized compounds exhibit high yields, excellent enantioselectivity, and moderate to good diastereoselectivity.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Inorganic & Nuclear
Olmo Lozano-Lavilla, Pablo Gomez-Orellana, Agusti Lledos, Juan A. Casares
Summary: The study found that the mechanism for the formation of homocoupling products when [Cu(bipy)(C6F5)] reacts with Rf-I mainly involves transmetalation from [Cu(bipy)(C6F5)] to Cu(III) intermediates formed in the oxidative addition step. Density functional theory calculations showed that the interaction between these Cu(III) species and the starting Cu(I) complex involves a Cu(I)-Cu(III) electron transfer and the formation of an iodine bridge between the metals.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jie Lin, Minqiang Jia, Shengming Ma
Summary: The paper presents the successful development of the palladium-catalyzed exclusive 2,3-allenylation reaction of oxindoles with 2,3-allenylic carbonates, along with a proposed rationale for the selectivity of this reaction over the expected 1,3-alkadienylation.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Review
Chemistry, Inorganic & Nuclear
Archana Rajmane, Sanjay Jadhav, Arjun Kumbhar
Summary: Pd-catalyzed cross-coupling reactions are crucial in achieving valuable organic transformations, and recent developments have focused on phosphine-free ligands such as N-heterocyclic carbenes and amines, which offer broad scope and environmental friendliness.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shuai Zhao, Xiang-Xiang Chen, Nan Gao, Mingcheng Qian, Xin Chen
Summary: The cyclopropanation reaction of 3-diazooxindoles with arenes was successfully achieved for the first time using visible-light irradiation, leading to the synthesis of a series of spiro[norcaradiene-7,3'-indolin]-2'-ones with high yields and excellent diastereoselectivities. The synthetic utility of this catalyst-free photochemical methodology was further demonstrated through controllable rearrangement and epoxidation reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Archana Rajmane, Arjun Kumbhar
Summary: In recent years, Pd-catalyzed cross-coupling reactions have been widely used in various fields of chemistry. However, traditional phosphine ligands used in these reactions have limitations. Therefore, phosphine-free ligands and mixed donor P, N-ligands have attracted attention for their advantages in catalysis.
MOLECULAR CATALYSIS
(2022)
Review
Chemistry, Inorganic & Nuclear
Jeffery Wee Kiong Seah, Ronald Hong Xiang Teo, Pak-Hing Leung
Summary: Palladacycles with chiral chelating auxiliaries have been proven to be efficient catalysts for asymmetric hydrophosphination reactions, with the chiral auxiliaries remaining coordinated to the palladium centers during reactions and showing little susceptibility to catalyst poisoning. The unique stereoelectronic features and organometallic chemistry of palladacycle catalysts are essential for their synthetic operations.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Multidisciplinary
Caio C. Oliveira, Carlos Roque Duarte Correia
Summary: This article highlights the significance of the enantioselective palladium-catalyzed Heck-Matsuda reaction in the evolution of synthetic methods, as well as the interesting discoveries and synthetic opportunities that have emerged from our laboratory in this field.
Article
Chemistry, Multidisciplinary
Eric D. Kalkman, John F. Hartwig
Summary: The study focuses on the Pd-catalyzed asymmetric alpha-arylation of carbonyl compounds, investigating the stereoselectivity and reactivity of arylpalladium enolate intermediates. It reveals that the rate of reductive elimination impacts the enantioselectivity significantly and that complexes with more electron-rich aryl ligands react faster. Noncovalent interactions stabilize the pathway to the major product enantiomer more strongly than to the minor enantiomer.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Siou-Wei Liang, Yingjie Guo, Wan-Ching Lee, Pin-Rui Zeng, Tzu-Hao Lin, Pei-Zhen Xie, Hsuan-Hao Kang, I-Chung Lu, Yu-Chang Chang
Summary: Two newly designed Pd(II) precatalysts were synthesized and used to efficiently convert unreactive aryl chlorides, benzyl chlorides, and benzoyl chlorides. The deprotonation of the precatalysts led to the dissociation of NHC, and the proposed Pd(II) species could be reduced to Pd(0) using ethoxide. The size of salt additive cations and the basicity of the base were found to influence the catalytic properties.
Article
Chemistry, Multidisciplinary
Liang-Yong Mei, Yin Wei, Xiang-Ying Tang, Min Shi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Multidisciplinary
Hai Yang, Liangyong Mei, Pengcheng Wang, Joseph Genereux, Yinsheng Wang, Bing Yi, Chaktong Au, Limin Dang, Pingyun Feng
Article
Chemistry, Organic
Liang-Yong Mei, Xiang-Ying Tang, Min Shi
ORGANIC & BIOMOLECULAR CHEMISTRY
(2014)
Review
Chemistry, Multidisciplinary
Hannah Goodman, Liangyong Mei, Thomas L. Gianetti
FRONTIERS IN CHEMISTRY
(2019)
Article
Biochemical Research Methods
Liangyong Mei, Maureen R. Montoya, Guy M. Quanrud, Minh Tran, Athena Villa-Sharma, Ming Huang, Joseph C. Genereux
JOURNAL OF PROTEOME RESEARCH
(2020)
Article
Chemistry, Multidisciplinary
Liangyong Mei, Jose M. Veleta, Thomas L. Gianetti
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Organic
Liangyong Mei, Thomas Gianetti
Summary: A sustainable catalytic system for red-light-induced photocatalysis has been developed, utilizing a helical carbenium ion-based organic photoredox catalyst. This versatile and efficient catalyst is capable of using low-energy red light for both photooxidations and photoreductions, showing successful applications in various reactions like oxidative hydroxylation and C-H bond oxidation.
Article
Chemistry, Organic
Liangyong Mei, Jules Moutet, Savannah M. Stull, Thomas L. Gianetti
Summary: A red-light-mediated cascade intramolecular trifluoromethylation and dearomatization reaction has been developed for the synthesis of 3,3-spirocyclic indolines with Umemoto's reagent. This protocol provides a facile and efficient approach with moderate to high yields and excellent diastereoselectivities. Mechanistic studies support the formation of crucial species such as CF3 radical and a dearomatized benzyl carbocation intermediate.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Analytical
Guy M. Quanrud, Maureen R. Montoya, Liangyong Mei, Mohammad R. Awad, Joseph C. Genereux
Summary: This study developed a quantitative proteomics methodology to identify destabilized proteins based on their binding to the human Hsp40 chaperone DNAJB8. Exposure of HEK293T cells to meta-arsenite increased the affinity of certain proteins to DNAJB8, including the pyruvate dehydrogenase complex E1 subunit and several RNA-binding proteins. The platform can be used to investigate the impact of environmental toxins on cellular proteostasis and identify susceptible proteins.
ANALYTICAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Savannah M. Stull, Liangyong Mei, Thomas L. Gianetti
Summary: A new organic reaction method has been reported in this study, allowing for the synthesis of a variety of organic molecules under mild conditions. This method can effectively produce cyclopentane or cyclopentene derivatives with different functional groups.
Article
Biochemistry & Molecular Biology
Ziqi Lyu, Melody M. Sycks, Mateo F. Espinoza, Khanh K. Nguyen, Maureen R. Montoya, Cheska M. Galapate, Liangyong Mei, Joseph C. Genereux
Summary: Protein mistargeting can threaten cellular protein homeostasis, but current measurement methods are difficult to apply to living cells. This study uses genetically encoded peroxidases to investigate protein import into the endoplasmic reticulum (ER) and demonstrates that proximity labeling is an effective strategy for characterizing factors that influence ER protein import in living cells.
ACS CHEMICAL BIOLOGY
(2022)
Review
Chemistry, Organic
Alexander H. Schade, Liangyong Mei
Summary: Photoredox catalysis is a highly efficient and versatile approach for developing novel synthetic methodologies. Red light photocatalysis, in particular, has gained more attention due to its advantages of low energy, few health risks, few side reactions, and high penetration depth. This review outlines the applications of different photoredox catalysts in a wide range of red light-mediated reactions, as well as provides an overview of NIR-induced reactions and the advantages of red light and NIR photoredox catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Liangyong Mei, Jose M. Veleta, Jan Bloch, Hannah J. Goodman, Dominic Pierce-Navarro, Alejandro Villalobos, Thomas L. Gianetti
DALTON TRANSACTIONS
(2020)
Article
Chemistry, Multidisciplinary
Bo Cao, Liang-Yong Mei, Xiao-Ge Li, Min Shi
