Interrupting the [Au]-catalyzed nitroalkyne cycloisomerization: trapping the putative alpha-oxo gold carbene with benzo[c]isoxazole

TitleInterrupting the [Au]-catalyzed nitroalkyne cycloisomerization: trapping the putative alpha-oxo gold carbene with benzo[c]isoxazole
Publication TypeJournal Article
Year of Publication2021
AuthorsDhote, PS, ,
JournalOrganic Letters
Volume23
Issue7
Pagination2632-2637
Date PublishedAPR
Type of ArticleArticle
ISSN1523-7060
Abstract

The [Au]-catalyzed nitroalkyne cycloisomerization of 2-alkynylnitrobenzenes leading to anthranils has been interrupted by possible trapping of the postulated intermediate alpha-oxo gold carbene with an external nucleophile such as benzo[c]isoxazole (anthranil). At the outset, this provides a simple synthesis of highly functionalized 3-acyl-(2-formylphenyl)-2H-indazoles with the sequential C-O, C-N, and N-N bond formations. This provides indirect support for the existence of alpha-oxo gold carbenes in the [Au]-catalyzed internal redox processes of nitroalkynes.

DOI10.1021/acs.orglett.1c00539
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)6.005
Divison category: 
Organic Chemistry

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