Please use this identifier to cite or link to this item:
Title: Expedient synthesis of heterocycles and methyl sulfonyl compounds via C-X BONDS (X = O, N, S) construction
Authors: Jiang, Yaojia
Keywords: DRNTU::Science::Chemistry
Issue Date: 2014
Source: Jiang, Y. (2014). Expedient synthesis of heterocycles and methyl sulfonyl compounds via C-X BONDS (X = O, N, S) construction. Doctoral thesis, Nanyang Technological University, Singapore.
Abstract: In this thesis, we have described new strategies for the synthesis of heterocycles including furans, 2H-azirines, pyrroles, and pyridines through construction of C–O and C–N bonds, respectively as well as novel approaches to synthesis of methyl sulfonyl compounds including β-keto methyl sulfones and (E)-vinyl methyl sulfones through C–S bond construction. In chapter 1, we have described diverse transformations of α-diazo-β-keto compounds into furans and 2H-azirines in the presence of transition metal catalysts. In chapter 2, we have described two methodologies for the synthesis of highly substituted pyrroles from a common substrate, α-diazo-β-keto oxime ethers, involving 2-vinyl-2H-azirines as key intermediates. In chapter 3, we have described two methodologies to synthesize multi-substituted pyridines from rhodium-catalyzed nitrene reaction and DBU-mediated ring opening of 2-allyl-2H-azirines. In chapter 4, we have described a radical strategy promoted by copper, oxygen and HPO(OEt)2 for the difunctionalization of alkenes to synthesize β-keto methyl sulfones; meanwhile, we have also demonstrated that alkynes could be directly undergo methyl sulfonylation to afford (E)-vinyl methyl sulfones through modification of the reaction condition.
DOI: 10.32657/10356/62203
Schools: School of Physical and Mathematical Sciences 
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Theses

Files in This Item:
File Description SizeFormat 
THESIS-Yaojia Jiang.pdfMain text of thesis7.81 MBAdobe PDFThumbnail

Page view(s)

Updated on Dec 9, 2023

Download(s) 5

Updated on Dec 9, 2023

Google ScholarTM




Items in DR-NTU are protected by copyright, with all rights reserved, unless otherwise indicated.