A silver-catalyzed tandem carbon!carbon triple bond hydroazidation, radical addition, and cyclization of biphenyl acetylene is described under mild conditions, leading to the formation of 6-methyl sulfonylated phenanthridines in good yields. In this novel cascade reaction, most of the atoms are incorporated into the product without cleavage of the CC bond. Mechanistic studies suggest the reaction should proceed through an iminyl radical reactive intermediate.

Silver-Catalyzed Tandem C=C Bond Hydroazidation/Radical Addition/Cyclization of Biphenyl Acetylene: One-Pot Synthesis of 6-Methyl Sulfonylated Phenanthridines

Zanoni, Giuseppe
Conceptualization
;
2017-01-01

Abstract

A silver-catalyzed tandem carbon!carbon triple bond hydroazidation, radical addition, and cyclization of biphenyl acetylene is described under mild conditions, leading to the formation of 6-methyl sulfonylated phenanthridines in good yields. In this novel cascade reaction, most of the atoms are incorporated into the product without cleavage of the CC bond. Mechanistic studies suggest the reaction should proceed through an iminyl radical reactive intermediate.
2017
The Organic Chemistry/Polymer Science category includes resources concerned with the related fields of organic chemistry and polymer science. The organic chemistry resources deal with compounds of carbon with the exception of certain simple ones, such as the carbon oxides, carbonates, cyanides and cyanates (see Inorganic & Nuclear Chemistry). This category includes research on synthetic and natural organic compounds that may include other elements, such as hydrogen and oxygen, but also nitrogen, halogens, sulphur and phosphorous. Resources concerned with hydrocarbons, organic compounds containing only the elements carbon and hydrogen, are also included in this category. Examples are the alkanes, alkenes, alkynes and aromatics, such as benzene and naphthalene. Polymer science includes all resources dealing with the study, production and technology of polymers, which are compounds composed of very large molecules made up of repeating molecular units (monomers). Polymers may be natural substances, such as polysaccharides or proteins, or synthetic materials, such as nylon or polyethylene.
Inglese
Internazionale
STAMPA
19
15
4026
4029
4
Biochemistry; Physical and Theoretical Chemistry; Organic Chemistry
http://pubs.acs.org/journal/orlef7
5
info:eu-repo/semantics/article
262
Tang, Jiawei; Sivaguru, Paramasivam; Ning, Yongquan; Zanoni, Giuseppe; Bi, Xihe
1 Contributo su Rivista::1.1 Articolo in rivista
open
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/1211191
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