1859-39-8

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 68, p. 9865, 2003 DOI: 10.1021/jo035351l

InChI:InChI=1/C14H11NO/c16-15-13-9-5-4-8-12(13)10-14(15)11-6-2-1-3-7-11/h1-10,16H

Upstream product

• 100-42-5 styrene 
• 577-19-5 2-nitrophenyl bromide 
• 4264-29-3 (E)-2-nitrostilbene 
• 35010-17-4 1-nitro-2-phenylethynyl-benzene 
• 536-74-3 phenylacetylene 
• 4212-33-3 2-(2-nitrophenyl)-1-phenylethanone 
• 4714-25-4 2-nitrostilbene 

Downstream Products

• 1969-74-0 2-phenylisatogen 
• 58810-39-2 2-phenyl-1H-indol-1-yl benzoate 
• 64968-19-0 1-hydroxy-2-phenyl-3-(2-quinolyl)indole 
• 64968-18-9 1-benzoyloxy-2-phenyl-3-(2-quinolyl)indole 
• 6016-57-5 2-phenyl-3-(2-quinolyl)indole 
• 948-65-2 2-phenyl-indole 
• 16616-82-3 1-methoxy-2-phenylindole 
• 37914-49-1 2-phenyl-1H-indol-1-yl 4-nitrobenzoate 
• 79697-28-2 2-(2-phenyl-3-indolyl)cyclohexanol 
• 3469-20-3 2,3-diphenyl-1H-indole 
• 57152-69-9 2-phenyl-1H-indol-3-yl benzoate 
• 5169-64-2 1,1'-dihydroxy-2,2'-diphenyl-3,3'-biindole 
• 2196-95-4 2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide 
• 58535-63-0 1'-hydroxy-2,2'-diphenyl-1,2-dihydro-1'H-[2,3']biindolyl-3-one 

Relevant academic research and scientific papers

A General Synthesis of N-Hydroxyindoles

A general method for the formation of N-hydroxyindoles is demonstrated through a lead-promoted intramolecular reductive cyclization of o-nitrobenzyl ketones and aldehydes under transfer hydrogenation conditions. The N-hydroxyindoles are isolated in high purity and excellent yield (> 90%) in an operationally simple procedure. This new method is exemplified by a two-step synthesis of the naturally occurring 1-methoxyindole-3-carboxaldehyde, which is pivotal in many alkaloid total syntheses.

Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles

tert-Butoxide unlocks new reactivity patterns embedded in nitroarenes. Exposure of nitrostilbenes to sodium tert-butoxide was found to produce N-hydroxyindoles at room temperature without an additive. Changing the counterion to potassium changed the reaction outcome to yield solely oxindoles through an unprecedented dioxygen-transfer reaction followed by a 1,2-phenyl migration. Mechanistic experiments established that these reactions proceed via radical intermediates and suggest that counterion coordination controls whether an oxindole or N-hydroxyindole product is formed.

Iron-Catalyzed Reductive Cyclization of o-Nitrostyrenes Using Phenylsilane as the Terminal Reductant

Using microscale high-throughput experimentation, an efficient, earth-abundant iron phenanthroline complex was discovered to catalyze the reductive cyclization of ortho-nitrostyrenes into indoles via nitrosoarene reactive intermediates. This method requires only 1 mol % of Fe(OAc)2 and 1 mol % of 4,7-(MeO)2phen and uses phenylsilane as a convenient terminal reductant. The scope and limitations of the method were illustrated with 21 examples, and an investigation into the kinetics of the reaction revealed first-order behavior in catalyst and silane and zero-order behavior with respect to nitrostyrene.

Reductive cyclizations of nitroarenes to hydroxamic acids by visible light photoredox catalysis

We have developed a photocatalytic reduction of nitroarenes as an efficient, chemoselective route to biologically important N-phenyl hydroxamic acid scaffolds. Optimal conditions call for 2.5 mol% of a ruthenium photocatalyst, visible light irradiation, and a dihydropyridine terminal reductant. Because of the mild nature of the visible light activation, functional groups that might be sensitive to other non-photochemical reduction methods are easily tolerated. Georg Thieme Verlag Stuttgart New York.