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RESEARCH PAPER · Angewandte Chemie International Edition · 2024

Stereodivergent, Kinetically Controlled Isomerization of Terminal Alkenes via Nickel Catalysis

Camille Rubel, Anne K. Ravn, Hang Chi Ho, Shenghua Yang, Zi‐Qi Li, Keary M. Engle, Julien C. Vantourout

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Stereodivergent, Kinetically Controlled Isomerization of Terminal Alkenes via Nickel CatalysisOriginalSelective C–H activation of unprotected allylamines by control of catalyst speciation7Tuneable, in situ -generated nickel-hydride alkene isomerisation catalyst0Alkene Isomerization Using a Heterogeneous Nickel-Hydride Catalyst27Nickel-hydrogen-bonding-enabled, phosphine-ligand-tuned regiodivergent isomerization of olefins6Phosphine ligand-dependent nickel-catalyzed regiodivergent isomerization of alkenes2( Z )-Selective Isomerization of 1,1-Disubstituted Alkenes by Scandium-Catalyzed Allylic C–H Activation25Access to Alkenyl Cyclobutanols by Ni‐Catalyzed Regio‐ and Enantio‐Selective syn ‐Hydrometalative 4‐ exo ‐ trig Cyclization of Alkynones12Access to Alkenyl Cyclobutanols by Ni‐Catalyzed Regio‐ and Enantio‐Selective syn ‐Hydrometalative 4‐ exo ‐ trig Cyclization of Alkynones0Tungsten-catalyzed stereodivergent isomerization of terminal olefins7Co( ii )-catalyzed isomerization of enals using hydrogen atom transfer0Recent developments in organic synthesis for constructing carbon frameworks using transposition strategies7Deprotonative Functionalization of Allylic C(sp³)-H Bonds with N-tert-Butyl-N'-Silyldiazenes0Trendbericht: Organische Chemie 20250Halogen‐Atom Transfer Enabled Z‐Selective Styrene Synthesis via Dual Cobalt and Photocatalysis Through Coupling of Unactivated Alkyl Iodides With Terminal Arylalkynes6Halogen‐Atom Transfer Enabled Z‐Selective Styrene Synthesis via Dual Cobalt and Photocatalysis Through Coupling of Unactivated Alkyl Iodides With Terminal Arylalkynes0Flash Communication: Oxidative Addition of 3-Iodopyridine at a Nickel Diphosphine Complex: Probing Secondary Borane Effects0Proton-Modulated Nickel Hydride Electrocatalysis for the Hydrogenation of Unsaturated Bonds and Olefin Isomerization23Stereospecific positional alkene isomerization enables bidirectional central-to-axial chirality transfer12Water-Driven Isomerization Control: Dinuclear Cobalt-Catalyzed Monoisomerization of Linear Terminal Alkenes2Stereo-reversed E2 unlocks Z -selective C–H functionalization21Iron‐Catalyzed Tunable Double Bond Migration and Geometrical Isomerization in Olefins via a Spin‐Accelerated Alkyl Mechanism4Equivalent Atrop- and Positional Isomerism in Styrene Derivatives Prepared by Enantioselective 1,3-Diarylation4Ligand-controlled stereodivergent proton migration in skipped enynes0Olefin isomerisation–metathesis (ISOMET): recent advances in sustainable applications0An anionic nickel-aluminium dihydride complex exhibiting cooperative catalytic behaviour1Highly regio- and E -stereoselective CC bond transposition catalyzed by tris(benzhydryl) sodium calciate. Proof of synergy: one metal is good, but two are better0Native photoreactivity-enabled ruthenium-catalyzed scalable alkene isomerization0Positional isomerization of N -allyl compounds with a practical low-valent cobalt catalyst system0Recent progress in proton-based hydrogen sources for nickel(0)-catalyzed hydrofunctionalization: advances and perspectives0Mechanistic Insights into Nickel–NHC-Catalyzed Alkene Isomerization: A Computational Study on Selectivity and Reactivity1Aryl Halide-Driven Nickel Photocatalytic Decarboxylative Elimination5Synthesis Side Stories: Capitalizing the Unintended Side‐Product1Iron-catalyzed alkene isomerization and tandem functionalization1Catalytic, Regioselective Hydrocarbofunctionalization of Unactivated Alkenes with Anthrones and 9-Phenanthrols0Photoinduced Nickel Catalysis for the Z ‐Selective Monoisomerization of Terminal Alkenes0Photochemical Cobalt-Catalyzed Selective Olefin Hydrogenation and One-Bond Transposition0Nickel-Catalyzed β-Methyl Vinylation Using Allylamine as a Masked Alkenyl Electrophile0

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  1. Selective C–H activation of unprotected allylamines by control of catalyst speciation

    Chem Catalysis · 2023-11-01

    Vinod Gokulkrishna Landge, Ankita Mishra, Waruna Thotamune, Audrey L. Bonds, Indunil Alahakoon, Ajith Karunarathne, Michael C. Young

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  2. Tuneable, in situ -generated nickel-hydride alkene isomerisation catalyst

    Catalysis Science & Technology · 2024-01-01

    Melanie A. Kascoutas, Alison Sy-min Chang, Kiana E. Kawamura, Gabriela Bailey, Parker T. Morris, Elizabeth Borst, Lilliana Granados, Amanda K. Cook

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  3. Alkene Isomerization Using a Heterogeneous Nickel-Hydride Catalyst

    Journal of the American Chemical Society · 2024-05-21

    Alison Sy-min Chang, Melanie A. Kascoutas, Quinn P. Valentine, Kiera How, Rachel Thomas, Amanda K. Cook

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  4. Nickel-hydrogen-bonding-enabled, phosphine-ligand-tuned regiodivergent isomerization of olefins

    Chem Catalysis · 2024-07-04

    Shuang Yan Yang, Qi Zhang, Hui Chen, Da Chuan Zhao, Yang Wang

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  5. Phosphine ligand-dependent nickel-catalyzed regiodivergent isomerization of alkenes

    Chem Catalysis · 2024-08-01

    Jinping Wang, Peng George Wang

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  6. ( Z )-Selective Isomerization of 1,1-Disubstituted Alkenes by Scandium-Catalyzed Allylic C–H Activation

    Journal of the American Chemical Society · 2024-09-20

    Shao‐Jie Lou, Pan Wang, Xin Wen, Aniket Mishra, Xuefeng Cong, Qingde Zhuo, Kun An, Masayoshi Nishiura, Yi Luo, Zhaomin Hou

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  7. Access to Alkenyl Cyclobutanols by Ni‐Catalyzed Regio‐ and Enantio‐Selective syn ‐Hydrometalative 4‐ exo ‐ trig Cyclization of Alkynones

    Angewandte Chemie International Edition · 2024-10-11

    Xiao‐Lin Li, Jiang‐Lian Deng, Jian Long, Yiyi Fu, Yu-Qing Zheng, Wen‐Bo Liu

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  8. Access to Alkenyl Cyclobutanols by Ni‐Catalyzed Regio‐ and Enantio‐Selective syn ‐Hydrometalative 4‐ exo ‐ trig Cyclization of Alkynones

    Angewandte Chemie · 2024-10-11

    Xiao‐Lin Li, Jiang‐Lian Deng, Jian Long, Yi‐Fan Fu, Yu-Qing Zheng, Wen‐Bo Liu

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  9. Tungsten-catalyzed stereodivergent isomerization of terminal olefins

    Chemical Science · 2024-12-04

    Tanner C. Jankins, Camille Rubel, Hang Chi Ho, Raúl Martín‐Montero, Keary M. Engle

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  10. Co( ii )-catalyzed isomerization of enals using hydrogen atom transfer

    Chemical Communications · 2025-01-01

    Qiqige Qiqige, Edward Richmond, Rocco Paciello, Mathias Schelwies, Rylan J. Lundgren

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  11. Recent developments in organic synthesis for constructing carbon frameworks using transposition strategies

    Organic Chemistry Frontiers · 2025-01-01

    Savita Gat, Piyusa Priyadarsan Pattanaik, Rambabu Dandela

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  12. Deprotonative Functionalization of Allylic C(sp³)-H Bonds with N-tert-Butyl-N'-Silyldiazenes

    Unknown journal · 2025-02-17

    XueYan Zhang

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  13. Trendbericht: Organische Chemie 2025

    Nachrichten aus der Chemie · 2025-02-28

    Martin Breugst, Jennifer N. Andexer, Lena Barra, Sebastian B. Beil, Sascha Bierbach, Immo Burkhardt, Oliver Dumele∞, Martin Ernst, Jennifer Frommer, Urs Gellrich, Philipp Germer, Michael Giese, Peter Huy, Julian Klepp, Karsten Körber, Markus Kordes, Christian A. Kuttruff, Thomas Lindel, Fabian Pfrengle, Bartholomäus Pieber, Jörg Pietruszka, Norbert Schaschke, Mathias O. Senge, Nina Stadler, Golo Storch, Johannes F. Teichert, Siegfried R. Waldvogel, Thomas Werner, Christian Winter

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  14. Halogen‐Atom Transfer Enabled Z‐Selective Styrene Synthesis via Dual Cobalt and Photocatalysis Through Coupling of Unactivated Alkyl Iodides With Terminal Arylalkynes

    Angewandte Chemie International Edition · 2025-04-02

    Anxiang Huang, Zhao Liu, Ruobin Wang, Xinran Chang, Mingxing Feng, Yuxin Xiang, Xiaotian Qi, Jun Zhu

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  15. Halogen‐Atom Transfer Enabled Z‐Selective Styrene Synthesis via Dual Cobalt and Photocatalysis Through Coupling of Unactivated Alkyl Iodides With Terminal Arylalkynes

    Angewandte Chemie · 2025-04-02

    Anxiang Huang, Liu Zhao, Ruobin Wang, Xinran Chang, Mingxing Feng, Yuxin Xiang, Xiaotian Qi, Jun Zhu

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  16. Flash Communication: Oxidative Addition of 3-Iodopyridine at a Nickel Diphosphine Complex: Probing Secondary Borane Effects

    Organometallics · 2025-04-09

    Brady J. H. Austen, Marcus W. Drover

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  17. Proton-Modulated Nickel Hydride Electrocatalysis for the Hydrogenation of Unsaturated Bonds and Olefin Isomerization

    Journal of the American Chemical Society · 2025-04-22

    Xue Song, Yuanqiong Huang, Bei Zhao, Hanshuo Wu, Xiaotian Qi, Jianchun Wang

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  18. Stereospecific positional alkene isomerization enables bidirectional central-to-axial chirality transfer

    Nature Communications · 2025-07-23

    Qi Liu, Jun Gu, Hongfeng Zhuang, Ying He

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  19. Water-Driven Isomerization Control: Dinuclear Cobalt-Catalyzed Monoisomerization of Linear Terminal Alkenes

    Organometallics · 2025-07-31

    Gao‐Yin Wang, Hongdan Zhu, Yuyang Xu, Ke Chen, Jiayi Lin, Qian Peng, Xiaoming Wang

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  20. Stereo-reversed E2 unlocks Z -selective C–H functionalization

    Science · 2025-09-18

    Peter J. Verardi, Elizabeth A. Ryutov, Poulami Mukherjee, Rémy F. Lalisse, Karina Targos, Tetsuya Inagaki, Megan Kelly, Ilia A. Guzei, Marcel Schreier, Osvaldo Gutiérrez, Zachary K. Wickens

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  21. Iron‐Catalyzed Tunable Double Bond Migration and Geometrical Isomerization in Olefins via a Spin‐Accelerated Alkyl Mechanism

    Angewandte Chemie International Edition · 2025-10-16

    Abdul‐Halim Obeid, Christian Herrero, Régis Guillot, Jérôme Hannedouche

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  22. Equivalent Atrop- and Positional Isomerism in Styrene Derivatives Prepared by Enantioselective 1,3-Diarylation

    Journal of the American Chemical Society · 2025-10-22

    Amit Kumar Simlandy, Yiyao Hu, Turki M. Alturaifi, Wen‐Ji He, Madeline J. Fitzgerald, Peng Liu, Keary M. Engle

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  23. Ligand-controlled stereodivergent proton migration in skipped enynes

    Cell Reports Physical Science · 2025-12-01

    Tianle Wu, Chunying Fan, Weiwei Jin, Xiaowei Xie, Shaohong Wang, Huishuang Wang, Guangrui Shi, Yuchen Gao, Jiajia Sun, Yunyi Zhao, Yohei Shimizu, Motomu Kanai, Kristin Aslaug Persson, Pengchen Ma, Xiaofeng Wei

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  24. Olefin isomerisation–metathesis (ISOMET): recent advances in sustainable applications

    Royal Society of Chemistry eBooks · 2025-12-17

    Gábor Turczel, Ádám Erdélyi, Márton Nagyházi, Róbert Tuba

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  25. An anionic nickel-aluminium dihydride complex exhibiting cooperative catalytic behaviour

    Chemical Science · 2026-01-01

    Roel L. M. Bienenmann, Luca Vedani, Andryj M. Borys, Wilhelm Klein, Eva Hevia

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  26. Highly regio- and E -stereoselective CC bond transposition catalyzed by tris(benzhydryl) sodium calciate. Proof of synergy: one metal is good, but two are better

    Chemical Science · 2026-01-01

    Ivan V. Koshelev, Alexander N. Selikhov, Anton V. Cherkasov, Rinat R. Aysin, Alexander A. Trifonov

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  27. Native photoreactivity-enabled ruthenium-catalyzed scalable alkene isomerization

    Green Chemistry · 2026-01-01

    Hang Gu, Jun-Quan Miu, Fanfan Wang, Djike Tchuente Berol Loik, Weiping Su, Shao‐Fei Ni, Xiaoming Jie

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  28. Positional isomerization of N -allyl compounds with a practical low-valent cobalt catalyst system

    Organic & Biomolecular Chemistry · 2026-01-01

    Branislav Kokić, Ljiljana Koračak, Marina Pećinar, Timothy R. Newhouse, Bogdan A. Šolaja, Vladimir Ajdačić, Igor Opsenica

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  29. Recent progress in proton-based hydrogen sources for nickel(0)-catalyzed hydrofunctionalization: advances and perspectives

    Organic Chemistry Frontiers · 2026-01-01

    Heng-shuo Liu, Hua-Feng Cao, Ji-Xuan Zhang, Shengnan Jin, Giulio Goti, Sara Cuadros, ZhongYan Cao

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  30. Mechanistic Insights into Nickel–NHC-Catalyzed Alkene Isomerization: A Computational Study on Selectivity and Reactivity

    Organometallics · 2026-01-15

    Arslan Ahmad, Roger Monreal‐Corona, Arijit Saha, Anna Pla‐Quintana, Sergio Posada‐Pérez, Albert Poater

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  31. Aryl Halide-Driven Nickel Photocatalytic Decarboxylative Elimination

    ACS Catalysis · 2026-02-22

    Ning Wei, Sebastian B. Beil

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  32. Synthesis Side Stories: Capitalizing the Unintended Side‐Product

    Helvetica Chimica Acta · 2026-03-31

    Clara Massol‐Frieh, Julien C. Vantourout

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  33. Iron-catalyzed alkene isomerization and tandem functionalization

    Communications Chemistry · 2026-04-24

    Rohit Kumar, Anirban Sen, Tanuja Tewari, Suhas T. Parit, Kishor V. Khopade, Samir H. Chikkali

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  34. Catalytic, Regioselective Hydrocarbofunctionalization of Unactivated Alkenes with Anthrones and 9-Phenanthrols

    The Journal of Organic Chemistry · 2026-07-07

    Zhifeng Mao

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  35. Photoinduced Nickel Catalysis for the Z ‐Selective Monoisomerization of Terminal Alkenes

    Advanced Synthesis & Catalysis · 2026-07-12

    Kazuki Tamiya, Yuu Komori, Kosuke Higashida, Tatsuhiko Yoshino, Shigeki Matsunaga

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  36. Photochemical Cobalt-Catalyzed Selective Olefin Hydrogenation and One-Bond Transposition

    ACS Catalysis · 2026-08-14

    Ziheng Jian, Yujing Lin, Xiang Hao, Min Zhang, Zehuai Mou, Huifei Wang

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  37. Nickel-Catalyzed β-Methyl Vinylation Using Allylamine as a Masked Alkenyl Electrophile

    ACS Catalysis · 2026-09-25

    Ahyeon Cho, Yihan Tang, Jaehan Bae, Eun Jin Cho

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