Part I: Iron (III)-catalyzed reactions of benzylic analogs with organosilanes & Conia-ene cyclization. Part II: Palladium (II)-catalyzed C-H functionalizations using mono-phosphoric acid directing group
The use of transition metals as catalyst in mediating organic reactions is inevitable. In the first part of the thesis, we discussed thoroughly the usage of cheap and environmentally friendly iron(III) catalyst in promoting reactions of (i) benzylic acetates with organosilanes; (ii) reductive dehydr...
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| Format: | Thesis |
| Language: | English |
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2014
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| Online Access: | https://hdl.handle.net/10356/59859 |
| _version_ | 1824455269321539584 |
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| author | Chan, Li Yan |
| author2 | Kim Sung Gak |
| author_facet | Kim Sung Gak Chan, Li Yan |
| author_sort | Chan, Li Yan |
| collection | NTU |
| description | The use of transition metals as catalyst in mediating organic reactions is inevitable. In the first part of the thesis, we discussed thoroughly the usage of cheap and environmentally friendly iron(III) catalyst in promoting reactions of (i) benzylic acetates with organosilanes; (ii) reductive dehydroxylation of benzylic alcohols with polymethylhydrosiloxane; and (iii) the Conia-ene cyclization of 2-alkynic 1,3-dicarbonyl compounds. Ample works were done which demonstrated the efficiency of iron catalyst in these areas of organic synthesis chemistry. In the second part, a novel mono-phosphoric acid directing group was used to facilitate palladium(II)-catalyzed C-H functionalization reactions, that occurred in high selectivity at the ortho-position. The phosphate directing ability was proven in (i) ortho-alkenylation; (ii) ortho-arylation; and (iii) ortho-acetoxylation of aryl hydrogen phosphates. The palladium catalytic system could tolerate a broad range of functional groups, hence making this an attractive method to synthesis valuable functionalized arenes, which are common motifs of natural products. |
| first_indexed | 2025-02-19T03:35:31Z |
| format | Thesis |
| id | ntu-10356/59859 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2025-02-19T03:35:31Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-10356/598592023-02-28T23:59:19Z Part I: Iron (III)-catalyzed reactions of benzylic analogs with organosilanes & Conia-ene cyclization. Part II: Palladium (II)-catalyzed C-H functionalizations using mono-phosphoric acid directing group Chan, Li Yan Kim Sung Gak School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis The use of transition metals as catalyst in mediating organic reactions is inevitable. In the first part of the thesis, we discussed thoroughly the usage of cheap and environmentally friendly iron(III) catalyst in promoting reactions of (i) benzylic acetates with organosilanes; (ii) reductive dehydroxylation of benzylic alcohols with polymethylhydrosiloxane; and (iii) the Conia-ene cyclization of 2-alkynic 1,3-dicarbonyl compounds. Ample works were done which demonstrated the efficiency of iron catalyst in these areas of organic synthesis chemistry. In the second part, a novel mono-phosphoric acid directing group was used to facilitate palladium(II)-catalyzed C-H functionalization reactions, that occurred in high selectivity at the ortho-position. The phosphate directing ability was proven in (i) ortho-alkenylation; (ii) ortho-arylation; and (iii) ortho-acetoxylation of aryl hydrogen phosphates. The palladium catalytic system could tolerate a broad range of functional groups, hence making this an attractive method to synthesis valuable functionalized arenes, which are common motifs of natural products. DOCTOR OF PHILOSOPHY (SPMS) 2014-05-16T03:06:11Z 2014-05-16T03:06:11Z 2014 2014 Thesis Chan, L. Y. (2013). Part I: Iron (III)-catalyzed reactions of benzylic analogs with organosilanes & Conia-ene cyclization. Part II: Palladium (II)-catalyzed C-H functionalizations using mono-phosphoric acid directing group. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/59859 10.32657/10356/59859 en 186 p. application/pdf |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Chan, Li Yan Part I: Iron (III)-catalyzed reactions of benzylic analogs with organosilanes & Conia-ene cyclization. Part II: Palladium (II)-catalyzed C-H functionalizations using mono-phosphoric acid directing group |
| title | Part I: Iron (III)-catalyzed reactions of benzylic analogs with organosilanes & Conia-ene cyclization. Part II: Palladium (II)-catalyzed C-H functionalizations using mono-phosphoric acid directing group |
| title_full | Part I: Iron (III)-catalyzed reactions of benzylic analogs with organosilanes & Conia-ene cyclization. Part II: Palladium (II)-catalyzed C-H functionalizations using mono-phosphoric acid directing group |
| title_fullStr | Part I: Iron (III)-catalyzed reactions of benzylic analogs with organosilanes & Conia-ene cyclization. Part II: Palladium (II)-catalyzed C-H functionalizations using mono-phosphoric acid directing group |
| title_full_unstemmed | Part I: Iron (III)-catalyzed reactions of benzylic analogs with organosilanes & Conia-ene cyclization. Part II: Palladium (II)-catalyzed C-H functionalizations using mono-phosphoric acid directing group |
| title_short | Part I: Iron (III)-catalyzed reactions of benzylic analogs with organosilanes & Conia-ene cyclization. Part II: Palladium (II)-catalyzed C-H functionalizations using mono-phosphoric acid directing group |
| title_sort | part i iron iii catalyzed reactions of benzylic analogs with organosilanes conia ene cyclization part ii palladium ii catalyzed c h functionalizations using mono phosphoric acid directing group |
| topic | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis |
| url | https://hdl.handle.net/10356/59859 |
| work_keys_str_mv | AT chanliyan partiironiiicatalyzedreactionsofbenzylicanalogswithorganosilanesconiaenecyclizationpartiipalladiumiicatalyzedchfunctionalizationsusingmonophosphoricaciddirectinggroup |