Zinc-Catalyzed Alkyne Oxidation/CH Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines
An efficient zinc(II)‐catalyzed alkyne oxidation/CH functionalization sequence was developed, thus leading to highly site‐selective synthesis of a variety of isoquinolones and β‐carbolines. Importantly, in contrast to the well‐established gold‐catalyzed intermolecular alkyne oxidation, over‐oxidati...
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| Published in | Angewandte Chemie International Edition Vol. 54; no. 28; pp. 8245 - 8249 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
06.07.2015
WILEY‐VCH Verlag |
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| Online Access | Get full text |
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| Abstract | An efficient zinc(II)‐catalyzed alkyne oxidation/CH functionalization sequence was developed, thus leading to highly site‐selective synthesis of a variety of isoquinolones and β‐carbolines. Importantly, in contrast to the well‐established gold‐catalyzed intermolecular alkyne oxidation, over‐oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel–Crafts‐type pathway. Mechanistic studies and theoretical calculations are described.
Swap gold for zinc: The title reaction was achieved by a zinc(II)‐catalyzed alkyne oxidation/CH functionalization sequence. In contrast to the well‐established gold‐catalyzed intermolecular alkyne oxidation, the over‐oxidation can be suppressed in this system and the reaction most likely proceeds by a Friedel–Crafts‐type pathway. Tf=trifluoromethanesulfonyl, PG=protecting group. |
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| AbstractList | An efficient zinc(II)-catalyzed alkyne oxidation/C-H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of isoquinolones and β-carbolines. Importantly, in contrast to the well-established gold-catalyzed intermolecular alkyne oxidation, over-oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theoretical calculations are described.An efficient zinc(II)-catalyzed alkyne oxidation/C-H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of isoquinolones and β-carbolines. Importantly, in contrast to the well-established gold-catalyzed intermolecular alkyne oxidation, over-oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theoretical calculations are described. An efficient zinc(II)-catalyzed alkyne oxidation/C-H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of isoquinolones and β-carbolines. Importantly, in contrast to the well-established gold-catalyzed intermolecular alkyne oxidation, over-oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theoretical calculations are described. An efficient zinc(II)‐catalyzed alkyne oxidation/CH functionalization sequence was developed, thus leading to highly site‐selective synthesis of a variety of isoquinolones and β‐carbolines. Importantly, in contrast to the well‐established gold‐catalyzed intermolecular alkyne oxidation, over‐oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel–Crafts‐type pathway. Mechanistic studies and theoretical calculations are described. Swap gold for zinc: The title reaction was achieved by a zinc(II)‐catalyzed alkyne oxidation/CH functionalization sequence. In contrast to the well‐established gold‐catalyzed intermolecular alkyne oxidation, the over‐oxidation can be suppressed in this system and the reaction most likely proceeds by a Friedel–Crafts‐type pathway. Tf=trifluoromethanesulfonyl, PG=protecting group. An efficient zinc(II)‐catalyzed alkyne oxidation/CH functionalization sequence was developed, thus leading to highly site‐selective synthesis of a variety of isoquinolones and β‐carbolines. Importantly, in contrast to the well‐established gold‐catalyzed intermolecular alkyne oxidation, over‐oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel–Crafts‐type pathway. Mechanistic studies and theoretical calculations are described. |
| Author | Zhou, Bo Pan, Yi-Fei Li, Long Wang, Yong-Heng Ye, Long-Wu Shu, Chao Lu, Xin |
| Author_xml | – sequence: 1 givenname: Long surname: Li fullname: Li, Long organization: State Key Laboratory for Physical Chemistry of Solid Surfaces & The Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, Xiamen University, Xiamen 361005 (China) – sequence: 2 givenname: Bo surname: Zhou fullname: Zhou, Bo organization: State Key Laboratory for Physical Chemistry of Solid Surfaces & The Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, Xiamen University, Xiamen 361005 (China) – sequence: 3 givenname: Yong-Heng surname: Wang fullname: Wang, Yong-Heng organization: State Key Laboratory of Physical Chemistry of Solid Surfaces & Center for Theoretical Chemistry, Department of Chemistry, Xiamen University, Xiamen 361005 (China) – sequence: 4 givenname: Chao surname: Shu fullname: Shu, Chao organization: State Key Laboratory for Physical Chemistry of Solid Surfaces & The Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, Xiamen University, Xiamen 361005 (China) – sequence: 5 givenname: Yi-Fei surname: Pan fullname: Pan, Yi-Fei organization: State Key Laboratory for Physical Chemistry of Solid Surfaces & The Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, Xiamen University, Xiamen 361005 (China) – sequence: 6 givenname: Xin surname: Lu fullname: Lu, Xin email: xinlu@xmu.edu.cn organization: State Key Laboratory of Physical Chemistry of Solid Surfaces & Center for Theoretical Chemistry, Department of Chemistry, Xiamen University, Xiamen 361005 (China) – sequence: 7 givenname: Long-Wu surname: Ye fullname: Ye, Long-Wu email: longwuye@xmu.edu.cn organization: State Key Laboratory for Physical Chemistry of Solid Surfaces & The Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, Xiamen University, Xiamen 361005 (China) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26013998$$D View this record in MEDLINE/PubMed |
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| Keywords | homogeneous catalysis heterocycles zinc nitrogen oxides synthetic methods |
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| Snippet | An efficient zinc(II)‐catalyzed alkyne oxidation/CH functionalization sequence was developed, thus leading to highly site‐selective synthesis of a variety of... An efficient zinc(II)-catalyzed alkyne oxidation/C-H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of... |
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| SubjectTerms | Acids, Heterocyclic - chemistry Carbolines - chemistry Catalysis heterocycles homogeneous catalysis nitrogen oxides Nitrogen Oxides - chemistry Oxidation-Reduction synthetic methods zinc Zinc - chemistry |
| Title | Zinc-Catalyzed Alkyne Oxidation/CH Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines |
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