Tin-free radical mediated C-C bond formation via the Xanthate transfer
Formation of carbon-carbon bonds had been by far the most researched and refined objective in organic synthesis. On the contrary, the use of free-radical chemistry in this area had thus been limited to tin-mediated protocols which were gradually losing popularity due to toxicity and purification iss...
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sg-ntu-dr.10356-629482023-02-28T23:44:39Z Tin-free radical mediated C-C bond formation via the Xanthate transfer Goh, Kelvin Kau Kiat Loh Teck Peng School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Formation of carbon-carbon bonds had been by far the most researched and refined objective in organic synthesis. On the contrary, the use of free-radical chemistry in this area had thus been limited to tin-mediated protocols which were gradually losing popularity due to toxicity and purification issues. Xanthates, a class of thiocarbonylthio compounds have found remarkable application in both inter- and intra-molecular tin-free radical additions to simple and un-activated olefins. In this thesis, the use of xanthates is further explored and renewed through combination with other types of radical chemistry previously employed with tin-based initiators. The goal is to develop novel tin-free solutions in the C-C bond formation for the synthesis of highly functionalized molecules which had otherwise been plagued by acid-base problems in ionic chemistry. This concept is briefly demonstrated by a few free-radical alternatives to enolate chemistry involving ketones, lactones and thiolactones. DOCTOR OF PHILOSOPHY (SPMS) 2015-05-04T04:42:57Z 2015-05-04T04:42:57Z 2015 2015 Thesis Goh, K. K. K. (2015). Tin-free radical mediated C-C bond formation via the Xanthate transfer. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/62948 10.32657/10356/62948 en 595 p. application/pdf |
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DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Goh, Kelvin Kau Kiat Tin-free radical mediated C-C bond formation via the Xanthate transfer |
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Formation of carbon-carbon bonds had been by far the most researched and refined objective in organic synthesis. On the contrary, the use of free-radical chemistry in this area had thus been limited to tin-mediated protocols which were gradually losing popularity due to toxicity and purification issues. Xanthates, a class of thiocarbonylthio compounds have found remarkable application in both inter- and intra-molecular tin-free radical additions to simple and un-activated olefins. In this thesis, the use of xanthates is further explored and renewed through combination with other types of radical chemistry previously employed with tin-based initiators. The goal is to develop novel tin-free solutions in the C-C bond formation for the synthesis of highly functionalized molecules which had otherwise been plagued by acid-base problems in ionic chemistry. This concept is briefly demonstrated by a few free-radical alternatives to enolate chemistry involving ketones, lactones and thiolactones. |
author2 |
Loh Teck Peng |
author_facet |
Loh Teck Peng Goh, Kelvin Kau Kiat |
format |
Theses and Dissertations |
author |
Goh, Kelvin Kau Kiat |
author_sort |
Goh, Kelvin Kau Kiat |
title |
Tin-free radical mediated C-C bond formation via the Xanthate transfer |
title_short |
Tin-free radical mediated C-C bond formation via the Xanthate transfer |
title_full |
Tin-free radical mediated C-C bond formation via the Xanthate transfer |
title_fullStr |
Tin-free radical mediated C-C bond formation via the Xanthate transfer |
title_full_unstemmed |
Tin-free radical mediated C-C bond formation via the Xanthate transfer |
title_sort |
tin-free radical mediated c-c bond formation via the xanthate transfer |
publishDate |
2015 |
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https://hdl.handle.net/10356/62948 |
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1759855366637617152 |