18648-69-6

Upstream product

• 530-48-3 1,1-Diphenylethylene 
• 119-66-4 2-nitrobenzenediazonium chloride 
• 18648-81-2 2-(2-nitro-phenyl)-4,4-diphenyl-[1,3]oxathiolan-5-one 
• 4214-38-4 (diphenylmethylene)triphenylphosphorane 
• 552-89-6 2-nitro-benzaldehyde 
• 3128-85-6 diphenylmethyl isocyanide 
• 612-23-7 2-nitrobenzyl chloride 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 54963-39-2 benzhydrylphosphinic acid dimethyl ester 
• 7333-65-5 (diphenylmethyl)triphenylphosphonium bromide 
• 776-74-9 Bromodiphenylmethane 
• 1444018-12-5 2,2-diphenylvinyl methanesulfonate 
• 15163-59-4 potassium o-nitrobenzoate 
• 947-91-1 Diphenylacetaldehyde 

Downstream Products

• 805188-34-5 2-(2,2-diphenylvinyl)-phenylamine 
• 3469-20-3 2,3-diphenyl-1H-indole 
• 57309-24-7 1-hydroxy-2,2-diphenyl-indolin-3-one 

Relevant academic research and scientific papers

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.

Divergent Syntheses of Indoles and Quinolines Involving N1-C2-C3 Bond Formation through Two Distinct Pd Catalyses

Pd-catalyzed annulative couplings of 2-alkenylanilines with aldehydes using alcohols as both the solvent and hydrogen source have been developed. These domino processes allow divergent syntheses of two significant N-heterocycles, indoles and quinolines, from the same substrate by tuning reaction parameters, which seems to invoke two distinct mechanisms. The nature of the ligand and alcoholic solvent had a profound influence on the selectivity and efficiency of these protocols. Particularly noteworthy is that indole formation was achieved by overcoming two significant challenges, regioselective hydropalladation of alkenes and subsequent reactions between the resulting Csp3-Pd species and less reactive imines.

Palladium-Catalyzed Formation of N-Heteroarenes from Nitroarenes using Molybdenum Hexacarbonyl as the Source of Carbon Monoxide

The development of a method that employs a two-chamber reaction vessel and uses molybdenum hexacarbonyl [Mo(CO)6] as the carbon monoxide (CO) source for the palladium-catalyzed transformation of nitroarenes into indoles or imidazoles is reported.

Metal-free C-H amination for indole synthesis

An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.

Decarboxylative cross-coupling of mesylates catalyzed by copper/palladium systems with customized imidazolyl phosphine ligands

The activation of the inert C-O bonds in mesylates through the use of a new class of imidazolyl phosphines allows the decarboxylative coupling of aryl mesylates as well as polysubstituted alkenyl mesylates. Variation of the ligands leads to two complementary methods providing the corresponding biaryls and polysubstituted olefins in good yields. Copyright

Dirhodium(II)-catalyzed intramolecular C-H amination of aryl azides

(Chemical Equation Presented) Azides to indoles: Dirhodium(II)-catalyzed decomposition of aryl azides was developed as a mild, functional group tolerant method for the synthesis of indoles (see scheme).

β-Elimination of the Isonitrile Group in Alkylation Reactions of C-H Acids Activated by the Isonitrile Function

During phase-transfer alkylation of the isonitriles R1R2CHNC with X-CH2-Y, where X is a leaving group and Y an electron withdrawing group, some of the alkylation products undergo β-elimination of the isonitrile function to yield R1R2C=CHY.

REACTIONS OF ORGANIC ANIONS. PART C. PHASE-TRANSFER ALKYLATION OF C-H ACIDS ACTIVATED BY THE ISONITRILE FUNCTION. UNPRECENDENTED β-ELIMINATION OF THE ISONITRILE GROUP

Benzylation and nitrobenzylation reactions of isocyanides in a catalytic two-phase system and in some homolytic systems were studied.Elimination of the isocyanide group has been observed in the products obtained.