Developing a new phosphorus-carbon bond synthesis

This thesis is about developing a new phosphorus-carbon bond synthesis based on electrophilic terminal phosphinidene chemistry and finding application for this methodology. The first chapter gives a brief account of the general methods in forming phosphorus-carbon bonds. The second chapter details t...

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Main Author: Ng, Yong Xiang
Other Authors: Francois Mathey
Format: Theses and Dissertations
Language:English
Published: 2016
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Online Access:https://hdl.handle.net/10356/66040
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-660402023-02-28T23:51:27Z Developing a new phosphorus-carbon bond synthesis Ng, Yong Xiang Francois Mathey School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis This thesis is about developing a new phosphorus-carbon bond synthesis based on electrophilic terminal phosphinidene chemistry and finding application for this methodology. The first chapter gives a brief account of the general methods in forming phosphorus-carbon bonds. The second chapter details the works of the author on using the reaction of electrophilic terminal phosphinidene complexes with arylboronic acids in presence of potassium phosphate to form phosphorus-carbon bond. Preliminary mechanistic study was carried out, and the results tentatively suggest that the reaction proceeds via the insertion of phosphinidene complex into the boron-oxygen bond of arylboronic acid, followed by a 1,2-migration of the aryl group onto the phosphorus atom. The third chapter is based on exploring and expanding the scope and application for this new P-C bond. It was found out that the reaction pathway of terminal phosphinidene complexes and alkenylboronic acids can be altered by potassium phosphate. In the absence of phosphate, [1+2] cycloaddition proceeds to give phosphirane complexes; P-C bond formation proceeds in the presence of phosphate to give secondary alkenylphosphine complexes. Computations were made to understand this shift in reaction. Attempts to synthesise other organophosphorus compounds were also made. DOCTOR OF PHILOSOPHY (SPMS) 2016-03-04T03:03:45Z 2016-03-04T03:03:45Z 2016 Thesis Ng, Y. X. (2016). Developing a new phosphorus-carbon bond synthesis. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/66040 10.32657/10356/66040 en 202 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
spellingShingle DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Ng, Yong Xiang
Developing a new phosphorus-carbon bond synthesis
description This thesis is about developing a new phosphorus-carbon bond synthesis based on electrophilic terminal phosphinidene chemistry and finding application for this methodology. The first chapter gives a brief account of the general methods in forming phosphorus-carbon bonds. The second chapter details the works of the author on using the reaction of electrophilic terminal phosphinidene complexes with arylboronic acids in presence of potassium phosphate to form phosphorus-carbon bond. Preliminary mechanistic study was carried out, and the results tentatively suggest that the reaction proceeds via the insertion of phosphinidene complex into the boron-oxygen bond of arylboronic acid, followed by a 1,2-migration of the aryl group onto the phosphorus atom. The third chapter is based on exploring and expanding the scope and application for this new P-C bond. It was found out that the reaction pathway of terminal phosphinidene complexes and alkenylboronic acids can be altered by potassium phosphate. In the absence of phosphate, [1+2] cycloaddition proceeds to give phosphirane complexes; P-C bond formation proceeds in the presence of phosphate to give secondary alkenylphosphine complexes. Computations were made to understand this shift in reaction. Attempts to synthesise other organophosphorus compounds were also made.
author2 Francois Mathey
author_facet Francois Mathey
Ng, Yong Xiang
format Theses and Dissertations
author Ng, Yong Xiang
author_sort Ng, Yong Xiang
title Developing a new phosphorus-carbon bond synthesis
title_short Developing a new phosphorus-carbon bond synthesis
title_full Developing a new phosphorus-carbon bond synthesis
title_fullStr Developing a new phosphorus-carbon bond synthesis
title_full_unstemmed Developing a new phosphorus-carbon bond synthesis
title_sort developing a new phosphorus-carbon bond synthesis
publishDate 2016
url https://hdl.handle.net/10356/66040
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