Copper-catalyzed condensation reactions for the synthesis of multisubstituted heteroarenes
Heteroarenes are ubiquitously found in many biologically active natural and man made products such as pharmaceuticals, polymeric materials, and are also essential building blocks for the synthesis of complex molecules. Thus, the efficient and regioselective synthesis of heteroaromatic compounds...
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| Format: | Thesis |
| Language: | English |
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2017
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| Online Access: | http://hdl.handle.net/10356/72135 |
| _version_ | 1811682959742205952 |
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| author | Tan, Simon Wei Wen |
| author2 | Naohiko Yoshikai |
| author_facet | Naohiko Yoshikai Tan, Simon Wei Wen |
| author_sort | Tan, Simon Wei Wen |
| collection | NTU |
| description | Heteroarenes are ubiquitously found in many biologically active natural and man
made products such as pharmaceuticals, polymeric materials, and are also essential
building blocks for the synthesis of complex molecules. Thus, the efficient and
regioselective synthesis of heteroaromatic compounds has been one of the main topics of
interest for organic, medicinal and material chemists. Over the past decades, transition
metal catalysts have emerged to be attractive and powerful tools to enable heteroarene
synthesis with a broad functional group compatibility and unique reaction patterns, thus
complementing the limitations of classical synthetic methods.
This thesis describes the development of new copper-catalyzed condensation
methods for the synthesis of highly substituted heteroarenes such as pyrroles, furans,
thiophenes, and pyridines. Following the general introduction described in Chapter 1,
Chapter 2 describes a copper-catalyzed condensation of imines and diazocarbonyl
compounds to afford highly substituted pyrroles, which is also applicable to the synthesis
of lamellarin family of natural products. Chapter 3 describes an extension of the method
developed in Chapter 2, that is, a copper-catalyzed condensation of 2-siloxy-1-alkenes
and diazocarbonyl compounds into highly substituted 2-siloxy-2,3-dihydrofurans. The 2
siloxy-2,3-dihydrofurans serve as versatile surrogates for the preparation of furans,
pyrroles and thiophenes in one-pot. In Chapter 4, we have established a copper-catalyzed
condensation of O-acetyl oximes and α,β-unsaturated imines to afford highly substituted
pyridines. The reactions developed herein commonly feature simple and low cost
catalytic systems, broad functional group tolerance, regioselective formation of highly
substituted heteroarenes starting from readily available starting materials. |
| first_indexed | 2024-10-01T04:05:08Z |
| format | Thesis |
| id | ntu-10356/72135 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:05:08Z |
| publishDate | 2017 |
| record_format | dspace |
| spelling | ntu-10356/721352023-02-28T23:39:02Z Copper-catalyzed condensation reactions for the synthesis of multisubstituted heteroarenes Tan, Simon Wei Wen Naohiko Yoshikai School of Physical and Mathematical Sciences DRNTU::Science::Chemistry Heteroarenes are ubiquitously found in many biologically active natural and man made products such as pharmaceuticals, polymeric materials, and are also essential building blocks for the synthesis of complex molecules. Thus, the efficient and regioselective synthesis of heteroaromatic compounds has been one of the main topics of interest for organic, medicinal and material chemists. Over the past decades, transition metal catalysts have emerged to be attractive and powerful tools to enable heteroarene synthesis with a broad functional group compatibility and unique reaction patterns, thus complementing the limitations of classical synthetic methods. This thesis describes the development of new copper-catalyzed condensation methods for the synthesis of highly substituted heteroarenes such as pyrroles, furans, thiophenes, and pyridines. Following the general introduction described in Chapter 1, Chapter 2 describes a copper-catalyzed condensation of imines and diazocarbonyl compounds to afford highly substituted pyrroles, which is also applicable to the synthesis of lamellarin family of natural products. Chapter 3 describes an extension of the method developed in Chapter 2, that is, a copper-catalyzed condensation of 2-siloxy-1-alkenes and diazocarbonyl compounds into highly substituted 2-siloxy-2,3-dihydrofurans. The 2 siloxy-2,3-dihydrofurans serve as versatile surrogates for the preparation of furans, pyrroles and thiophenes in one-pot. In Chapter 4, we have established a copper-catalyzed condensation of O-acetyl oximes and α,β-unsaturated imines to afford highly substituted pyridines. The reactions developed herein commonly feature simple and low cost catalytic systems, broad functional group tolerance, regioselective formation of highly substituted heteroarenes starting from readily available starting materials. Doctor of Philosophy (SPMS) 2017-05-29T01:59:02Z 2017-05-29T01:59:02Z 2017 Thesis Tan, S. W. W. (2017). Copper-catalyzed condensation reactions for the synthesis of multisubstituted heteroarenes. Doctoral thesis, Nanyang Technological University, Singapore. http://hdl.handle.net/10356/72135 10.32657/10356/72135 en 172 p. application/pdf |
| spellingShingle | DRNTU::Science::Chemistry Tan, Simon Wei Wen Copper-catalyzed condensation reactions for the synthesis of multisubstituted heteroarenes |
| title | Copper-catalyzed condensation reactions for the synthesis of multisubstituted heteroarenes |
| title_full | Copper-catalyzed condensation reactions for the synthesis of multisubstituted heteroarenes |
| title_fullStr | Copper-catalyzed condensation reactions for the synthesis of multisubstituted heteroarenes |
| title_full_unstemmed | Copper-catalyzed condensation reactions for the synthesis of multisubstituted heteroarenes |
| title_short | Copper-catalyzed condensation reactions for the synthesis of multisubstituted heteroarenes |
| title_sort | copper catalyzed condensation reactions for the synthesis of multisubstituted heteroarenes |
| topic | DRNTU::Science::Chemistry |
| url | http://hdl.handle.net/10356/72135 |
| work_keys_str_mv | AT tansimonweiwen coppercatalyzedcondensationreactionsforthesynthesisofmultisubstitutedheteroarenes |