Palladium(II)‐Initiated Catellani‐Type Reactions
The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo‐fused rings, which are usually difficult to access through traditional cross‐coupling strategies. It utilizes the synergistic interplay of palladium and norbornene catalysis to...
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| Published in | Angewandte Chemie International Edition Vol. 58; no. 18; pp. 5832 - 5844 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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Germany
Wiley Subscription Services, Inc
23.04.2019
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| Edition | International ed. in English |
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| Online Access | Get full text |
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| Abstract | The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo‐fused rings, which are usually difficult to access through traditional cross‐coupling strategies. It utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho C−H functionalization and ipso termination of aryl halides in a single operation. In classical Catellani‐type reactions, aryl halides are mainly used as the substrates, and a Pd0 catalyst is required to initiate the reaction. Nevertheless, recent advances showcase that Catellani‐type reactions can also be initiated by a PdII catalyst with different starting materials instead of aryl halides via different reaction mechanisms and under different conditions. This emerging concept of PdII/norbornene cooperative catalysis has significantly advanced Catellani‐type reactions, thus enabling future developments of this field. In this Minireview, PdII‐initiated Catellani‐type reactions and their application in the synthesis of bioactive molecules are summarized.
Cooperative solutions: Palladium(II)‐initiated norbornene (NBE)‐mediated cooperative catalysis has enabled significant developments of the Catellani reaction. These advances and their application in the synthesis of bioactive molecules are summarized in this Minireview. |
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| AbstractList | The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo‐fused rings, which are usually difficult to access through traditional cross‐coupling strategies. It utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho C−H functionalization and ipso termination of aryl halides in a single operation. In classical Catellani‐type reactions, aryl halides are mainly used as the substrates, and a Pd0 catalyst is required to initiate the reaction. Nevertheless, recent advances showcase that Catellani‐type reactions can also be initiated by a PdII catalyst with different starting materials instead of aryl halides via different reaction mechanisms and under different conditions. This emerging concept of PdII/norbornene cooperative catalysis has significantly advanced Catellani‐type reactions, thus enabling future developments of this field. In this Minireview, PdII‐initiated Catellani‐type reactions and their application in the synthesis of bioactive molecules are summarized.
Cooperative solutions: Palladium(II)‐initiated norbornene (NBE)‐mediated cooperative catalysis has enabled significant developments of the Catellani reaction. These advances and their application in the synthesis of bioactive molecules are summarized in this Minireview. The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo-fused rings, which are usually difficult to access through traditional cross-coupling strategies. It utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho C-H functionalization and ipso termination of aryl halides in a single operation. In classical Catellani-type reactions, aryl halides are mainly used as the substrates, and a Pd catalyst is required to initiate the reaction. Nevertheless, recent advances showcase that Catellani-type reactions can also be initiated by a Pd catalyst with different starting materials instead of aryl halides via different reaction mechanisms and under different conditions. This emerging concept of Pd /norbornene cooperative catalysis has significantly advanced Catellani-type reactions, thus enabling future developments of this field. In this Minireview, Pd -initiated Catellani-type reactions and their application in the synthesis of bioactive molecules are summarized. The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo‐fused rings, which are usually difficult to access through traditional cross‐coupling strategies. It utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho C−H functionalization and ipso termination of aryl halides in a single operation. In classical Catellani‐type reactions, aryl halides are mainly used as the substrates, and a Pd0 catalyst is required to initiate the reaction. Nevertheless, recent advances showcase that Catellani‐type reactions can also be initiated by a PdII catalyst with different starting materials instead of aryl halides via different reaction mechanisms and under different conditions. This emerging concept of PdII/norbornene cooperative catalysis has significantly advanced Catellani‐type reactions, thus enabling future developments of this field. In this Minireview, PdII‐initiated Catellani‐type reactions and their application in the synthesis of bioactive molecules are summarized. The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo‐fused rings, which are usually difficult to access through traditional cross‐coupling strategies. It utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho C−H functionalization and ipso termination of aryl halides in a single operation. In classical Catellani‐type reactions, aryl halides are mainly used as the substrates, and a Pd 0 catalyst is required to initiate the reaction. Nevertheless, recent advances showcase that Catellani‐type reactions can also be initiated by a Pd II catalyst with different starting materials instead of aryl halides via different reaction mechanisms and under different conditions. This emerging concept of Pd II /norbornene cooperative catalysis has significantly advanced Catellani‐type reactions, thus enabling future developments of this field. In this Minireview, Pd II ‐initiated Catellani‐type reactions and their application in the synthesis of bioactive molecules are summarized. The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo-fused rings, which are usually difficult to access through traditional cross-coupling strategies. It utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho C-H functionalization and ipso termination of aryl halides in a single operation. In classical Catellani-type reactions, aryl halides are mainly used as the substrates, and a Pd0 catalyst is required to initiate the reaction. Nevertheless, recent advances showcase that Catellani-type reactions can also be initiated by a PdII catalyst with different starting materials instead of aryl halides via different reaction mechanisms and under different conditions. This emerging concept of PdII /norbornene cooperative catalysis has significantly advanced Catellani-type reactions, thus enabling future developments of this field. In this Minireview, PdII -initiated Catellani-type reactions and their application in the synthesis of bioactive molecules are summarized.The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo-fused rings, which are usually difficult to access through traditional cross-coupling strategies. It utilizes the synergistic interplay of palladium and norbornene catalysis to facilitate sequential ortho C-H functionalization and ipso termination of aryl halides in a single operation. In classical Catellani-type reactions, aryl halides are mainly used as the substrates, and a Pd0 catalyst is required to initiate the reaction. Nevertheless, recent advances showcase that Catellani-type reactions can also be initiated by a PdII catalyst with different starting materials instead of aryl halides via different reaction mechanisms and under different conditions. This emerging concept of PdII /norbornene cooperative catalysis has significantly advanced Catellani-type reactions, thus enabling future developments of this field. In this Minireview, PdII -initiated Catellani-type reactions and their application in the synthesis of bioactive molecules are summarized. |
| Author | Chen, Ruiming Chen, Shuqing Zhou, Qianghui Cheng, Hong‐Gang |
| Author_xml | – sequence: 1 givenname: Hong‐Gang surname: Cheng fullname: Cheng, Hong‐Gang organization: Wuhan University – sequence: 2 givenname: Shuqing surname: Chen fullname: Chen, Shuqing organization: Wuhan University – sequence: 3 givenname: Ruiming surname: Chen fullname: Chen, Ruiming organization: Wuhan University – sequence: 4 givenname: Qianghui orcidid: 0000-0002-8125-0380 surname: Zhou fullname: Zhou, Qianghui email: qhzhou@whu.edu.cn organization: Wuhan University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30589184$$D View this record in MEDLINE/PubMed |
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| ContentType | Journal Article |
| Copyright | 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. |
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| Keywords | C−H functionalization palladium catalysis Catellani reaction norbornene cooperative catalysis |
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| PublicationDateYYYYMMDD | 2019-04-23 |
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| PublicationDecade | 2010 |
| PublicationPlace | Germany |
| PublicationPlace_xml | – name: Germany – name: Weinheim |
| PublicationTitle | Angewandte Chemie International Edition |
| PublicationTitleAlternate | Angew Chem Int Ed Engl |
| PublicationYear | 2019 |
| Publisher | Wiley Subscription Services, Inc |
| Publisher_xml | – name: Wiley Subscription Services, Inc |
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| Snippet | The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo‐fused rings, which are usually... The Catellani reaction is known as a powerful strategy for the expeditious synthesis of highly substituted arenes and benzo-fused rings, which are usually... |
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| SubjectTerms | Aromatic compounds Catalysis Catalysts Catellani reaction Chemical synthesis cooperative catalysis Coupling (molecular) C−H functionalization Halides norbornene Palladium palladium catalysis Reaction mechanisms Substrates |
| Title | Palladium(II)‐Initiated Catellani‐Type Reactions |
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