Yongzheng Ding

University of Science and Technology of China

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Hanmin Huang

University of Science and Technology of China

Hanmin Huang

Gang Li

Wuhan University

Suchen Zou

University of Science and Technology of China

Shangda Li

Fujian Institute of Research on the Structure of Matter

Guoqing Yang

University of Science and Technology of China

Bingjian Gao

University of Science and Technology of China

Jiaqi Yan

China University of Mining and Technology

Zhihua Cai

Shihezi University

Guoying Zhang

Institute of Coal Chemistry

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Chinese Academy of Sciences

University of Science and Technology of China

University of Chinese Academy of Sciences

Fujian Institute of Research on the Structure of Matter

Fuzhou University

Hefei National Center for Physical Sciences at Nanoscale

Hefei University

Guizhou University

Academy of Scientific and Innovative Research

Indian Institute of Chemical Technology

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Carbonylative cycloaddition between two different alkenes enabled by reactive directing groups: expedited construction of bridged polycyclic skeletons

Chemical Communications (2020)

Bingjian Gao Suchen Zou Guoqing Yang Yongzheng Ding Hanmin Huang

A novel palladium-catalyzed highly selective hydrocarbonylative cycloaddition reaction with two different alkenes in the presence of CO enabled by a reactive directing-group is developed, which offers efficient and convenient access to lactone-containing bridged polycyclic compounds in high yield with high chemo- and stereoselectivities.

10.1039/d0cc05362g

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CCDC 1991852: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Bingjian Gao Suchen Zou Guoqing Yang Yongzheng Ding Hanmin Huang

10.5517/ccdc.csd.cc24vp90

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Copper-catalyzed oxidative amidation between aldehydes and arylamines under mild conditions

Tetrahedron Letters (2014)

Yongzheng Ding Xian Zhang Dongyang Zhang Yuting Chen Zhibing Wu

Amide

10.1016/j.tetlet.2014.12.113

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Taming Hydroxylamine for Carbonylative Cyclization of Aryl Alkynes to Isoquinolones via Isocyanate

CCS Chemistry (2025)

Jiaqi Yan Yongzheng Ding Yuyang Sun Hanmin Huang

Open AccessCCS ChemistryRESEARCH ARTICLES3 Feb 2025Taming Hydroxylamine for Carbonylative Cyclization of Aryl Alkynes to Isoquinolones via Isocyanate Jiaqi Yan, Yongzheng Ding, Yongna Sun and Hanmin Huang Jiaqi Yan , Yongzheng Ding , Yongna Sun and Hanmin Huang https://doi.org/10.31635/ccschem.025.202405250 SectionsSupplemental MaterialAboutPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail Organic isocyanates are versatile intermediates that provide access to a wide range of reactions. However, an efficient strategy to generate isocyanates from simple starting materials and control the reactivity has been a long-standing formidable challenge. Herein, we developed a novel palladium-catalyzed carbonylative approach that merges hydroaminocarbonylation with Lossen rearrangement to achieve alkenyl isocyanates, allowing for the rapid synthesis of isoquinolones that are of interest in synthetic organic and medicinal chemistry. Mechanistic studies disclosed for the first time that N-alkyloxylamides were generated as key intermediates and could undergo rearrangement like hydroxamic esters to deliver isocyanates, which represents a new type of Lossen rearrangement. The success of this reaction is attributed to the tamed sterically hindered O-substituent of hydroxylamines, which could efficiently suppress the side reactions and facilitate the Lossen rearrangement. Download figure Download PowerPoint Previous articleNext article FiguresReferencesRelatedDetails Issue AssignmentNot Yet AssignedSupporting Information Copyright & Permissions© 2025 Chinese Chemical Society Downloaded 14 times PDF downloadLoading ...

Hydroxylamine

Isocyanate

10.31635/ccschem.025.202405250

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CCDC 1990497: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Bingjian Gao Suchen Zou Guoqing Yang Yongzheng Ding Hanmin Huang

10.5517/ccdc.csd.cc24t8lv

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CCDC 2164075: Experimental Crystal Structure Determination

The Cambridge Structural Database (2022)

Min Si Jiaqi Yan Yongzheng Ding Hanmin Huang

10.5517/ccdc.csd.cc2bmwwr

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CCDC 1990501: Experimental Crystal Structure Determination

The Cambridge Structural Database (2020)

Bingjian Gao Suchen Zou Guoqing Yang Yongzheng Ding Hanmin Huang

10.5517/ccdc.csd.cc24t8qz

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CCDC 2127985: Experimental Crystal Structure Determination

The Cambridge Structural Database (2022)

Yongzheng Ding Hanmin Huang

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc29fbps

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The Development of Radical/Palladium Relay Catalysis for C–H Carbonylation

Synlett (2024)

Hanmin Huang Yongzheng Ding

The radical/palladium relay catalysis for C–H bonds carbonylation is an attractive research topic in synthetic chemistry. It can rapidly prepare carbonylated molecules for synthetic or pharmaceutical applications from highly sought-after feedstocks, such as alkylarenes, alkanes, alkenes or ethers. The main objective of this Synpacts article is to summarize the development of this research area, mainly focusing on radical/palladium relay catalysis for the carbonylation of single and double C-H bonds.

Carbonylation

10.1055/a-2413-0458

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Palladium-Catalyzed C(sp²)–H Olefination of Free Primary and Secondary 2-Phenylethylamines: Access to Tetrahydroisoquinolines

The Journal of Organic Chemistry (2019)

Shuai Fan Yongzheng Ding Xiaoxi Chen Yuzhen Gao Lei Fu

A rapid construction of THIQs by a Pd(II)-catalyzed C(sp2)–H olefination of free primary and secondary 2-phenylethylamines with high step- and atom-economy was reported. Notably, no substituent was required at the α-position to the amino group of the 2-phenylethylamines. The substrate scope was broad, and the reaction could also be applied to generate THIQs from the biologically active molecules such as the drug molecule baclofen and phenylalanine ester.

Primary (astronomy)

10.1021/acs.joc.9b01769

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Citations (16)