Article
Chemistry, Organic
Che-Ming Hsu, Shao-Chi Lee, Hao-En Tsai, Yong-Ting Tsao, Cheng-Lin Chan, Shinje Minoza, Zong-Nan Tsai, Li-Yun Li, Hsuan-Hung Liao
Summary: In this study, we successfully activated the C-S bond in sp(3)-hybridized thiols by introducing a per-/polyfluoroaryl moiety, enabling the efficient removal of sulfur groups and the generation of aliphatic radicals that can react with aryl halides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Regina M. Oechsner, Ivo H. Lindenmaier, Ivana Fleischer
Summary: We present a nickel catalyzed C-S cross-coupling reaction of aryl and alkenyl triflates with alkyl thiols. By using an air-stable nickel precatalyst, various thioethers could be synthesized under mild reaction conditions within a short reaction time. The reaction demonstrated a broad substrate scope, including pharmaceutically relevant compounds.
Article
Chemistry, Organic
Xinmiao Huang, Ling Tang, Zhiyong Song, Shuangshuang Jiang, Xianmao Liu, Ming Ma, Bo Chen, Yuanhong Ma
Summary: A nickel catalysis system has been developed for the desulfonylative C(sp(2))-C(sp(2)) reductive cross-coupling reactions of aryl sulfone derivatives with aryl bromides to form diverse biaryl compounds. The isolated and confirmed Ar-Ni(II)-SO(2)CF3 complex with a phosphine ligand through oxidative addition of aryl sulfone to Ni(0) species provides solid evidence for understanding the C(Ar)-SO2 bond activation and reaction mechanism.
Letter
Chemistry, Organic
Na-Na Ma, Xuan-Bo Hu, Yuan-Shuai Wu, Ya-Wen Zheng, Mengtao Ma, Xue-Qiang Chu, Hao Xu, Haiqing Luo, Zhi-Liang Shen
Summary: A direct cross-coupling reaction of aryl thioether with aryl bromide was successfully achieved using nickel salt, magnesium, and lithium chloride as catalysts in tetrahydrofuran solvent at room temperature. The one-pot reactions efficiently cleaved the C-S bond, yielding the desired biaryls in moderate to good yields, without the need for pregenerated or commercial organometallic reagents.
Article
Chemistry, Organic
Wen-Xin Li, Bo-Wen Yang, Xuan Ying, Zhuo-Wen Zhang, Xue-Qiang Chu, Xiaocong Zhou, Mengtao Ma, Zhi-Liang Shen
Summary: The direct cross-coupling of diaryl sulfoxides with aryl bromides via C-S bond cleavage was achieved using nickel(II) as the catalyst, 1,2-bis(diphenylphosphino)ethane (dppe) as the ligand, and magnesium turnings as the reducing metal in THF. This reaction showed a wide range of substrates and could be used for gram-scale synthesis. The one-pot reaction is operationally simple and economically efficient.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xuan-Di Song, Meng-Meng Guo, Shuang Xu, Chuanji Shen, Xiaocong Zhou, Xue-Qiang Chu, Mengtao Ma, Zhi-Liang Shen
Summary: A nickel-catalyzed direct reductive cross-coupling of disubstituted cycloalkyl iodides with aryl iodides was developed, allowing for efficient stereocontrolled synthesis of a variety of cross-coupled products with high diastereoselectivity and wide functional group tolerance. The one-pot reaction is simple to operate, providing a convenient method for the synthesis of complex molecules.
Article
Chemistry, Organic
Jin-He Na, Xiang Liu, Jia-Wen Jing, Jing Wang, Xue-Qiang Chu, Mengtao Ma, Hao Xu, Xiaocong Zhou, Zhi-Liang Shen
Summary: A step-economical and efficient one-pot reaction was developed for the direct cross-coupling of aryl fluorosulfate with aryl bromide. This reaction, conducted at room temperature in THF solvent, does not require the use of preprepared/commercial organometallic reagents. By utilizing nickel catalyst, magnesium turnings, and lithium chloride, the desired biaryls were obtained in moderate to good yields with reasonable functional group compatibility.
Article
Chemistry, Multidisciplinary
Raymond F. Turro, Julie L. H. Wahlman, Z. Jaron Tong, Xiahe Chen, Miao Yang, Emily P. Chen, Xin Hong, Ryan G. Hadt, K. N. Houk, Yun-Fang Yang, Sarah E. Reisman
Summary: Mechanistic investigations of the Ni-catalyzed asymmetric reductive alkenylation of N-hydroxyphthalimide (NHP) esters and benzylic chlorides were conducted. The study revealed divergent mechanisms for these related transformations, with the mechanism of C(sp(3)) activation changing depending on the reactants used. Kinetic experiments showed that the rate of NHP ester reduction can be tuned by changing the Lewis acid. Spectroscopic studies and DFT calculations provided insights into the catalyst resting state and the origin of enantioinduction for the Ni-BOX catalyst.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Xianqiang Kong, Yiyi Chen, Xiaohui Chen, Zheng-Xuan Lu, Wei Wang, Shao-Fei Ni, Zhong-Yan Cao
Summary: By combining electrocatalysis and nickel catalysis, a unified strategy has been applied to successfully achieve the decarboxylative cross-coupling of four types of alpha-oxocarboxylic acids and their derivatives with aryl trimethylammonium salts under mild conditions. Our strategy provides a practical way for preparing aryl ketones, amides, esters, or aldehydes.
Article
Chemistry, Organic
Guofu Zhang, Jing Wang, Chenfei Guan, Yiyong Zhao, Chengrong Ding
Summary: The synthesis of aryl phosphonates via nickel and palladium-catalyzed cross-coupling of aryl fluorosulfonates and phosphites is efficient and versatile, with good to excellent yields under mild conditions. This method can also directly convert phenols to aryl phosphonates, enhancing synthetic efficiency.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Zijian Li, Wenxuan Sun, Xianxu Wang, Luyang Li, Yong Zhang, Chao Li
Summary: This method utilizes alcohols and aryl bromides as coupling partners, combining anodic preparation and nickel catalysis to efficiently construct C(sp(2))-C(sp(3)) bonds. The nickel-catalyzed paired electrolysis reaction showcases a broad substrate scope suitable for the synthesis of multifunctional compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Qianqian Lu, Haixing Guan, Yan-En Wang, Dan Xiong, Tingzhi Lin, Fei Xue, Jianyou Mao
Summary: A visible-light-promoted nickel/photoredox-catalyzed reductive cross-coupling reaction between vinyl bromides and benzyl chlorides has been reported, enabling the synthesis of a diverse array of enantioenriched allylic centers in good yields and high enantioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lucie Finck, Martin Oestreich
Summary: This article presents a general strategy for the synthesis of azobenzenes through an unprecedented C(sp(2))-N(sp(2)) cross-coupling reaction, using masked diazenes and aryl bromides. The reaction allows for the efficient preparation of azoarenes decorated with two aryl groups, with no loss of dinitrogen.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Tingzhi Lin, Pengcheng Qian, Yan-En Wang, Mingjie Ou, Ning Cui, Yu Ye, Rui Hua, Dan Xiong, Fei Xue, Patrick J. Walsh, Jianyou Mao
Summary: A direct and convenient method for the synthesis of aryl/alkenyl alkyl ketones has been developed. This method overcomes the limitations of previous methods and avoids the use of organometallic reagents.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Guangwu Sun, Herui Liu, Xiu Wang, Wenbo Zhang, Wenjun Miao, Qinyu Luo, Bing Gao, Jinbo Hu
Summary: In this manuscript, a novel palladium-catalyzed coupling reaction between gem-difluoroalkenes and aryl boronic acids is reported, which yields bioactive indane-type ketones with an all-carbon alpha-quaternary center. The mechanism involves a water-induced defluorination and cross-coupling cascade pathway, supported by characterization and stoichiometric reactions of the key intermediates RCF2PdII. The use of vinyl difluoromethylene motif as an in situ carbonyl precursor is unprecedented in transition-metal-catalyzed coupling reactions, and it is expected to spark broad interest in ketone synthesis, fluoroalkene functionalization, and design of new synthetic protocols based on the unique reactivity of difluoroalkyl palladium(II) species.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Gustavo Frensch, Ricardo Labes, Celso Luiz Wosch, Laieli dos Santos Munaretto, Kahlil Schwanka Salome, Palimecio G. Guerrero, Francisco A. Marques
TETRAHEDRON LETTERS
(2016)
Article
Chemistry, Applied
Gustavo Frensch, Nusrah Hussain, Francisco A. Marques, Patrick J. Walsh
ADVANCED SYNTHESIS & CATALYSIS
(2014)
Article
Chemistry, Multidisciplinary
Nusrah Hussain, Gustavo Frensch, Jiadi Zhang, Patrick J. Walsh
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Article
Chemistry, Multidisciplinary
Francisco A. Marques, Scheila R. M. Zaleski, Sonia M. N. Lazzari, Gustavo Frensch, Grece A. Senhorini, Beatriz H. L. N. S. Maia, Armin Troeger, Wittko Francke, Edson T. Iede, Kenji Mori
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
(2011)
Article
Chemistry, Multidisciplinary
Francisco A. Marques, Gustavo Frensch, Scheila R. M. Zaleski, Noemi Nagata, Beatriz H. L. N. Sales Maia, Sonia M. N. Lazzari, Cesar A. Lenz, Arlene G. Correa
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
(2012)
Article
Chemistry, Multidisciplinary
Francisco A. Marques, Celso L. Wosch, Gustavo Frensch, Ricardo Labes, Beatriz H. L. N. S. Maia, Kahlil S. Salome, Andersson Barison, Palimecio G. Guerrero
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Organic
Cristiane Y. Kawasoko, Carlos E. D. Nazario, Amanda S. Santana, Luiz H. Viana, Gabriela R. Hurtado, Francisco A. Marques, Gustavo Frensch, Paulo R. de Oliveira, Palimecio G. Guerrero, Diego B. Carvalho, Adriano C. M. Baroni
TETRAHEDRON LETTERS
(2011)
Article
Biochemistry & Molecular Biology
Gustavo Frensch, Scheila R. M. Zaleski, Renan R. Schorr, Liliane G. Dantas, Marina Krasniak, Sonia M. N. Lazzari, Beatriz H. L. N. S. Maia, Francisco A. Marques
Summary: Coniferous trees of the genus Pinus produce oleoresin to defend themselves against herbivorous insects and pathogens attacking different parts of the plants. In Brazil, the banded pine weevil is an important pest of Pinus, causing death by interrupting sap circulation. The study analyzed the volatile compounds emitted by Pinus twigs and found that attacked plants produced different volatiles and were more attractive to the insects. Understanding these compounds may aid in the development of effective traps and prevention strategies.
Article
Biotechnology & Applied Microbiology
Vivian Rotuno Moure, Cristiane Fabricio, Gustavo Frensch, Francisco A. Marques, David Alexander Mitchell, Nadia Krieger
BIOCATALYSIS AND AGRICULTURAL BIOTECHNOLOGY
(2014)
Meeting Abstract
Chemistry, Multidisciplinary
Nusrah Hussain, Gustavo Frensch, Ana Bellomo, Jiadi Zhang, Patrick J. Walsh
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2013)
Meeting Abstract
Chemistry, Multidisciplinary
Nusrah Hussain, Gustavo Frensch, Ana Bellomo, Jiadi Zhang, Patrick J. Walsh
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2013)
Article
Chemistry, Organic
Francisco A. Marques, Marcos A. Oliveira, Gustavo Frensch, Beatriz Helena L. N. Sales Maia, Andersson Barison, Cesar A. Lenz, Palimecio G. Guerrero
LETTERS IN ORGANIC CHEMISTRY
(2011)
Article
Chemistry, Medicinal
Sayonara Mendes Silva, Simone Yae Abe, Fabio Seigi Murakami, Gustavo Frensch, Francisco A. Marques, Tomoe Nakashima
