Author
Nan Jiang
Bio: Nan Jiang is an academic researcher from Peking University. The author has contributed to research in topics: Tosyl & Diazo. The author has an hindex of 6, co-authored 11 publications receiving 292 citations.
Topics: Tosyl, Diazo, Aryl, Imine, Nucleophile
Papers
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TL;DR: In this article, the effect of catalysts on the migratory aptitude of 1,2-aryl over 1, 2-hydride migration was studied and a reaction mechanism involving a "bridged" phenonium ion was proposed.
101 citations
TL;DR: In this article, the condensation of acyldiazomethanes to aldehydes and imines can be promoted with catalytic amount of DBU, which gives β-hydroxy α-diazo carbonyl compounds.
77 citations
TL;DR: It was found that, in most cases, the diazo decomposition gave preferentially 1, 2-aryl migration product, but 1,2-hydride migration predominated when PhCO(2)Ag/Et(3)N was the catalytic system.
Abstract: A series of β-(N-tosyl)amino diazo carbonyl compounds have been prepared by nucleophilic condensation of N-tosylimines with acyldiazomethanes. The diazo decomposition of these diazo carbonyl compounds under various catalytic conditions, including Rh(II) carboxylates, Cu(I) and Cu(II) complexes, PhCO2Ag/Et3N, TsOH, and SnCl2·2H2O, has been investigated. It was found that, in most cases, the diazo decomposition gave preferentially 1,2-aryl migration product, but 1,2-hydride migration predominated when PhCO2Ag/Et3N was the catalytic system. Hammett correlation has been applied in the analysis of the electronic effects of 1,2-aryl migration. The factors that govern the migratory preference and the mechanistic aspects of the reaction are discussed.
61 citations
TL;DR: The α-diazophosphonate was added to aryl (N-tosyl)imine to give β-aryl β-(N-toyl)amino α-depositions as mentioned in this paper.
27 citations
TL;DR: The methyl diazoacetate and aryl (N-tosyl)imines can be transformed into syn or anti α-hydroxy β-amino esters with high diastereoselectivities in three steps, followed by oxidation with Oxone® to generate α-oxo esters.
24 citations
Cited by
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TL;DR: This work aims to demonstrate the efforts towards in-situ applicability of EMMARM, which aims to provide real-time information about the physical properties of EMTs and their applications in the context of drug discovery and development.
Abstract: Alan Ford,† Hugues Miel, Aoife Ring,† Catherine N. Slattery,† Anita R. Maguire,*,†,‡ and M. Anthony McKervey* †Department of Chemistry and ‡School of Pharmacy, Analytical and Biological Chemistry Research Facility, Synthesis and Solid State Pharmaceutical Centre, University College Cork, Cork, Ireland Almac Discovery Ltd., David Keir Building, Stranmillis Road, Belfast BT9 5AG, United Kingdom Almac Sciences Ltd., Almac House, 20 Seagoe Industrial Estate, Craigavon BT63 5QD, United Kingdom
1,051 citations
TL;DR: New developments of various reactions of α-diazocarbonyl compounds have been reviewed in this article, which primarily focuses on the literatures published since 2003, focusing on the literature published in 2003.
637 citations
TL;DR: A modification of the Sonogoshira coupling reaction employing an amidine base and a substoichiometric amount of water generates symmetrical and unsymmetrical bisarylethynylenes in one pot through in situ deprotection of trimethylsilylethunylene-added intermediates.
253 citations
TL;DR: This review covers the addition of diazo compounds to ketones to afford homologated ketones, either in the presence or in the absence of promoters or catalysts, commenting on the complex regiochemistry of the reaction and the nature of the catalysts and promoters.
Abstract: This review covers the addition of diazo compounds to ketones to afford homologated ketones, either in the presence or in the absence of promoters or catalysts. Reactions with diazoalkanes, aryldiazomethanes, trimethylsilyldiazomethane, α-diazo esters, and disubstituted diazo compounds are covered, commenting on the complex regiochemistry of the reaction and the nature of the catalysts and promoters. The recent reports on the enantioselective version of ketone homologation reactions are gathered in one section, followed by reports on the use of cyclic ketones ring expansion in total synthesis. Although the first reports of this reaction appeared in the literature almost one century ago, the recent achievements, in particular, for the asymmetric version, forecast the development of new breakthroughs in the synthetically valuable field of diazo chemistry.
220 citations
TL;DR: The nucleophilic addition reaction of diazo-compound derived anions or enolates with electrophilic C=O and C=N bonds have been summarized and diverse reactivities of the diazocarbonyl compounds bearing other functional groups are demonstrated.
209 citations