Article
Chemistry, Multidisciplinary
Ziyan Zhang, Vladimir Gevorgyan
Summary: A mild palladium hydride-catalyzed difunctionalization of conjugated dienes and enynes is reported. This method enables the chemoselectivity switch of the initial hydropalladation step by enhancing the hydricity of PdH species with visible light, allowing for cascade annulation of various easily available and abundant substrates, such as acrylic acids, acrylic amides, and Baylis-Hillman adducts, towards a wide range of alkenyl or alkynyl lactones, lactams, and tetrahydrofurans.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Dong-Ting Dai, Meng-Wei Yang, Zhi-Yuan Chen, Zi-Lu Wang, Yun-He Xu
Summary: An efficient palladium-catalyzed asymmetric synthesis of axially chiral conjugated dienes via alkenyl C-H olefination is reported. The corresponding atropisomeric styrenes were obtained with good yields and enantioselectivities. This synthetic strategy offers easy operation, mild reaction conditions, wide functionality tolerance, and high efficiency.
Article
Multidisciplinary Sciences
Samuel H. Newman-Stonebraker, Sleight R. Smith, Julia E. Borowski, Ellyn Peters, Tobias Gensch, Heather C. Johnson, Matthew S. Sigman, Abigail G. Doyle
Summary: In this study, a classification workflow using monodentate phosphine ligands was developed to identify reactivity cliffs in 11 Ni- and Pd-catalyzed cross-coupling datasets. The minimum percent buried volume descriptor was found to be a physically meaningful and predictive representation of ligand structure in catalysis.
Article
Chemistry, Multidisciplinary
Daniel Sowa Prendes, Florian Papp, Nagesh Sankaran, Nardana Sivendran, Frederike Beyer, Christian Merten, Lukas J. Goossen
Summary: Arylglycines, which are important pharmacophores in several top-selling drugs, can now be synthesized from abundant aryl chlorides using a Pd-catalyzed Schollkopf-type amino acid synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jie Huang, Ling-Ling Chen, Zhi-Min Chen
Summary: A palladium-catalyzed regioselective 1,2-alkynyl-carbonalization of conjugated dienes with ethynylbenziodazolone (EBZ) and indoles has been developed, providing easy access to various molecules containing alkenyl, alkynyl, and indole groups. The resulting products are also suitable for various derivatizations.
Article
Chemistry, Organic
Ke Li, Zhenjie Gan, Er-Qing Li, Zheng Duan
Summary: A novel phosphine-catalyzed (4 + 2) cyclization reaction has been reported for the generation of functionalized dihydropyran skeletons from electron-deficient conjugated dienes and enones. Mechanistic investigation reveals the formation of a new phosphonium zwitterion, which undergoes consecutive reactions. An asymmetric variant has also been developed through efficient and economical chiral phosphine catalysis.
Article
Chemistry, Multidisciplinary
Yaxin Zeng, Hui Yang, Jiayi Du, Qin Huang, Guoliang Huang, Ying Xia
Summary: The control of linear/branched selectivity in transition-metal catalyzed allyl-allyl cross-coupling reactions has been investigated in this study. It has been found that the terminal/internal regioselectivity can be switched by fine-tuning the rhodium catalytic system. Different types of 1,5-dienes are produced with good yields, exhibiting isomerized terminal, internal, and terminal regioselectivity.
Article
Chemistry, Organic
Subhash D. Tanpure, Paul R. Blakemore
Summary: 1,2,4-Trisubstituted 1,3-butadienes were synthesized in a stereocontrolled manner through carbenoid eliminative cross-coupling, yielding four geometric isomers of 4,7-dimethyl-1-phenylocta-3,5-diene with high stereospecificity. The configuration of the newly generated trisubstituted alkene component of the diene could be selectively installed in either (E)- or (Z)-configuration by varying carbenoid stereochemical pairing and/or the mode of the elimination stage.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiaoqin Ning, Yongke Chen, Qian Ye, Fangdong Hu, Ying Xia
Summary: A palladium-catalyzed cross-coupling reaction between cyclobutenone N-tosylhadrazones and organohalides has been developed. The reaction involves the generation of a strained allylpalladium intermediate and subsequent electrocyclic ring opening and β-hydride elimination to produce conjugated enynes and enallenes. The broad substrate scope, high yields, and tunable product diversity make this protocol potentially valuable in organic synthesis.
Review
Chemistry, Organic
Wang Yuchao, Liu Jinbiao, He Zhitao
Summary: This paper summarizes the development, advancements and mechanistic features of palladium-catalyzed asymmetric hydrofunctionalizations of conjugated dienes. Based on the types of allylic stereogenic centers constructed, the review is divided into six parts.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Tingting Yan, Kaki Raveendra Babu, Yong Wu, Yang Li, Yuhai Tang, Silong Xu
Summary: A phosphine-catalyzed olefinic cross-coupling reaction between benzyl halides and fumarates has been described, providing trisubstituted alkenes with good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael addition, water-assisted hydrogen transfer, and phosphine elimination.
Article
Chemistry, Multidisciplinary
Hui-Yi Yang, Liang-Quan Lin, Na-Qi Li, Zhi-Hui Ren, Zheng-Hui Guan
Summary: In this study, we reported a novel palladium-catalyzed selective branched 3,4-hydroaminocarbonylation of 1,3-dienes to synthesize beta,gamma-unsaturated amides. This reaction utilizes readily available starting materials and tolerates a wide range of functional groups, providing an easy and effective approach to access diverse alpha-substituted beta,gamma-unsaturated amides. Mechanistic investigations suggest that the hydropalladation of dienes is irreversible and the insertion of CO into the allyl-Pd species is likely the rate-limiting step.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Dezhi Lin, Yunfang Liu, Hongyu Yang, Xiao Zhang, Huaming Sun, Yajun Jian, Weiqiang Zhang, Jianming Yang, Ziwei Gao
Summary: This research presents a highly selective C-O activation approach for the synthesis of cross-conjugated enynones using alpha, beta-unsaturated triazine esters as acyl electrophiles. Under base and phosphine ligand-free conditions, NHC-Pd(II)-Allyl precatalyst alone efficiently catalyzed the cross-coupling reaction of alpha, beta-unsaturated triazine esters with terminal alkynes, yielding 31 cross-conjugated enynones with diverse functional groups. This method showcases the potential of triazine-mediated C-O activation for the preparation of highly functionalized ketones.
Article
Chemistry, Applied
Haixia Zhao, Yuchen Jiang, Tongqing Weng, Yongjia Shang, Jian Wang
Summary: A three component construction of conjugated 1,3-dienes bearing oxindoles or isoquinolinediones from alkenylated aryl iodides, allenes and diazo compounds via a palladium catalyzed sequential alkene/allene/carbenoid insertion reaction was developed. Three C-C bonds were formed in high order, offering access to multi-substituted dienes in high yields and up to > 20:1 E/Z selectivities. The reaction features excellent functional groups tolerance under mild conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Guang-Yan Xing, Ya-Cheng Zhu, Deng-Yuan Li, Pei-Nian Liu
Summary: On-surface synthesis, a powerful tool for atomically precise fabrication of low-dimensional carbon nanomaterials, has greatly enriched fundamental science and technology. Achieving high selectivity of covalent coupling reactions remains challenging due to the complicated reactivity of organic groups and irreversibility of covalent bonds. Only a few on-surface covalent coupling reactions are frequently used, and this Perspective focuses on the development and synthetic applications of on-surface cross-coupling reactions.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Physical
Viet D. Nguyen, Vu T. Nguyen, Graham C. Haug, Hang T. Dang, Hadi D. Arman, Walter C. Ermler, Oleg V. Larionov
Article
Multidisciplinary Sciences
Claire E. Stelly, Graham C. Haug, Kaitlyn M. Fonzi, Miriam A. Garcia, Sean C. Tritley, Alexa P. Magnon, Maria Alicia P. Ramos, Matthew J. Wanat
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2019)
Article
Chemistry, Physical
Vu T. Nguyen, Viet D. Nguyen, Graham C. Haug, Hang T. Dang, Shengfei Jin, Zhiliang Li, Carsten Flores-Hansen, Brenda S. Benavides, Hadi D. Arman, Oleg Larionov
Article
Chemistry, Physical
Shengfei Jin, Graham C. Haug, Vu T. Nguyen, Carsten Flores-Hansen, Hadi D. Arman, Oleg V. Larionov
Article
Chemistry, Multidisciplinary
Vu T. Nguyen, Viet D. Nguyen, Graham C. Haug, Ngan T. H. Vuong, Hang T. Dang, Hadi D. Arman, Oleg V. Larionov
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Shengfei Jin, Hang T. Dang, Graham C. Haug, Ru He, Viet D. Nguyen, Vu T. Nguyen, Hadi D. Arman, Kirk S. Schanze, Oleg V. Larionov
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Physical
Hang T. Dang, Graham C. Haug, Vu T. Nguyen, Ngan T. H. Vuong, Viet D. Nguyen, Hadi D. Arman, Oleg Larionov
Article
Chemistry, Multidisciplinary
Vu T. Nguyen, Graham C. Haug, Viet D. Nguyen, Ngan T. H. Vuong, Hadi D. Arman, Oleg V. Larionov
Summary: This study introduces a visible light-induced dual catalytic platform that enables a one-step access to sulfonamides and sulfonyl azides directly from carboxylic acids. The broad scope of this platform is achieved through the efficient conversion of carboxylic acids to sulfinic acids catalyzed by acridine photocatalysts, coupled with copper-catalyzed sulfur-nitrogen bond-forming cross-couplings.