Palladium-Catalyzed Dearomative Cyclocarbonylation by CN Bond Activation
A fundamentally novel approach to bioactive quinolizinones is based on the palladium‐catalyzed intramolecular cyclocarbonylation of allylamines. [Pd(Xantphos)I2], which features a very large bite angle, has been found to facilitate the rapid carbonylation of azaarene‐substituted allylamines into bio...
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| Published in | Angewandte Chemie International Edition Vol. 54; no. 37; pp. 10912 - 10916 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
07.09.2015
WILEY‐VCH Verlag |
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| Abstract | A fundamentally novel approach to bioactive quinolizinones is based on the palladium‐catalyzed intramolecular cyclocarbonylation of allylamines. [Pd(Xantphos)I2], which features a very large bite angle, has been found to facilitate the rapid carbonylation of azaarene‐substituted allylamines into bioactive quinolizinones in good to excellent yields. This transformation represents the first dearomative carbonylation and is proposed to proceed by palladium‐catalyzed CN bond activation, dearomatization, CO insertion, and a Heck reaction.
Dearomatization: A highly efficient dearomative cyclocarbonylation reaction proceeds by palladium‐catalyzed CN bond activation, dearomatization, CO insertion, and a Heck reaction. This transformation represents the first general catalytic method for the synthesis of valuable bioactive quinolizinones. |
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| AbstractList | A fundamentally novel approach to bioactive quinolizinones is based on the palladium‐catalyzed intramolecular cyclocarbonylation of allylamines. [Pd(Xantphos)I2], which features a very large bite angle, has been found to facilitate the rapid carbonylation of azaarene‐substituted allylamines into bioactive quinolizinones in good to excellent yields. This transformation represents the first dearomative carbonylation and is proposed to proceed by palladium‐catalyzed CN bond activation, dearomatization, CO insertion, and a Heck reaction.
Dearomatization: A highly efficient dearomative cyclocarbonylation reaction proceeds by palladium‐catalyzed CN bond activation, dearomatization, CO insertion, and a Heck reaction. This transformation represents the first general catalytic method for the synthesis of valuable bioactive quinolizinones. A fundamentally novel approach to bioactive quinolizinones is based on the palladium‐catalyzed intramolecular cyclocarbonylation of allylamines. [Pd(Xantphos)I 2 ], which features a very large bite angle, has been found to facilitate the rapid carbonylation of azaarene‐substituted allylamines into bioactive quinolizinones in good to excellent yields. This transformation represents the first dearomative carbonylation and is proposed to proceed by palladium‐catalyzed CN bond activation, dearomatization, CO insertion, and a Heck reaction. A fundamentally novel approach to bioactive quinolizinones is based on the palladium-catalyzed intramolecular cyclocarbonylation of allylamines. [Pd(Xantphos)I sub(2)], which features a very large bite angle, has been found to facilitate the rapid carbonylation of azaarene-substituted allylamines into bioactive quinolizinones in good to excellent yields. This transformation represents the first dearomative carbonylation and is proposed to proceed by palladium-catalyzed C--N bond activation, dearomatization, CO insertion, and a Heck reaction. Dearomatization: A highly efficient dearomative cyclocarbonylation reaction proceeds by palladium-catalyzed C--N bond activation, dearomatization, CO insertion, and a Heck reaction. This transformation represents the first general catalytic method for the synthesis of valuable bioactive quinolizinones. A fundamentally novel approach to bioactive quinolizinones is based on the palladium-catalyzed intramolecular cyclocarbonylation of allylamines. [Pd(Xantphos)I2 ], which features a very large bite angle, has been found to facilitate the rapid carbonylation of azaarene-substituted allylamines into bioactive quinolizinones in good to excellent yields. This transformation represents the first dearomative carbonylation and is proposed to proceed by palladium-catalyzed CN bond activation, dearomatization, CO insertion, and a Heck reaction. A fundamentally novel approach to bioactive quinolizinones is based on the palladium-catalyzed intramolecular cyclocarbonylation of allylamines. [Pd(Xantphos)I2 ], which features a very large bite angle, has been found to facilitate the rapid carbonylation of azaarene-substituted allylamines into bioactive quinolizinones in good to excellent yields. This transformation represents the first dearomative carbonylation and is proposed to proceed by palladium-catalyzed CN bond activation, dearomatization, CO insertion, and a Heck reaction.A fundamentally novel approach to bioactive quinolizinones is based on the palladium-catalyzed intramolecular cyclocarbonylation of allylamines. [Pd(Xantphos)I2 ], which features a very large bite angle, has been found to facilitate the rapid carbonylation of azaarene-substituted allylamines into bioactive quinolizinones in good to excellent yields. This transformation represents the first dearomative carbonylation and is proposed to proceed by palladium-catalyzed CN bond activation, dearomatization, CO insertion, and a Heck reaction. |
| Author | Yu, Hui Zhang, Guoying Huang, Hanmin |
| Author_xml | – sequence: 1 givenname: Hui surname: Yu fullname: Yu, Hui organization: State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 (China) – sequence: 2 givenname: Guoying surname: Zhang fullname: Zhang, Guoying organization: State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 (China) – sequence: 3 givenname: Hanmin surname: Huang fullname: Huang, Hanmin email: hmhuang@licp.cas.cn organization: State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000 (China) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26200664$$D View this record in MEDLINE/PubMed |
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| Keywords | CN activation palladium quinolizinones cyclocarbonylation dearomatization |
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| Snippet | A fundamentally novel approach to bioactive quinolizinones is based on the palladium‐catalyzed intramolecular cyclocarbonylation of allylamines.... A fundamentally novel approach to bioactive quinolizinones is based on the palladium‐catalyzed intramolecular cyclocarbonylation of allylamines. [Pd(Xantphos)I... A fundamentally novel approach to bioactive quinolizinones is based on the palladium-catalyzed intramolecular cyclocarbonylation of allylamines.... A fundamentally novel approach to bioactive quinolizinones is based on the palladium-catalyzed intramolecular cyclocarbonylation of allylamines. [Pd(Xantphos)I... |
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| SubjectTerms | Activation Biocompatibility Bonding Carbonyls Catalysis Cobalt Cyclization cyclocarbonylation CN activation dearomatization Insertion Ketones - chemistry palladium Palladium - chemistry quinolizinones Synthesis Transformations |
| Title | Palladium-Catalyzed Dearomative Cyclocarbonylation by CN Bond Activation |
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