66730-28-7

Upstream product

• 25611-78-3 (R,S)-1,2-diphenylethylamine 
• 98-88-4 benzoyl chloride 
• 573-34-2 2,4,5-triphenyloxazole 
• 27962-33-0 N-(diphenylmethylidene)-1,2-diphenylethylamine 
• 451-40-1 phenyl benzyl ketone 
• 3082-58-4 (-)-1,2-diphenylethylamine 
• 1589-82-8 phenylmagnesium bromide 
• 1485-70-7 N-benzylbenzamide 
• 60000-09-1 1,2-diphenyl-1-ethylamine hydrochloride 
• 100-51-6 benzyl alcohol 
• 100-42-5 styrene 
• 100-47-0 benzonitrile 
• 100-44-7 benzyl chloride 
• 77444-02-1 Methyl N-(2-chloro-1,2-diphenylethyl)carbamate 

Downstream Products

• 77988-83-1 N-(1,2-diphenylethyl)benzimidoyl chloride 
• 103-30-0 (E)-1,2-diphenyl-ethene 

Relevant academic research and scientific papers

Peroxidation of C-H bonds adjacent to an amide nitrogen atom under mild conditions

Under mild conditions, the oxidative functionalization of C-H bonds adjacent to an amide nitrogen atom was achieved. tert-Butylperoxyamido acetal was obtained in high yields and could be further converted into α-substituted amides by treatment with Grigna

Iron-catalyzed benzamide formation. Application to the synthesis of moclobemide

A convenient and user-friendly method to yield benzamides from primary and secondary amines and various benzylic alcohols in the presence of a cheap iron salt (FeCl2·4H2O) and tert-butylhydroperoxide (70% in water) as a stoichiometric oxidant is described. Control experiments indicated that this reaction might involve radical species. This method proved to be general, generating a family of 30 benzamides and was applied to the preparative synthesis of anti-anxiety drug moclobemide.

Iron-catalyzed benzamide formation. Application to the synthesis of moclobemide

A convenient and user-friendly method to yield benzamides from primary and secondary amines and various benzylic alcohols in the presence of a cheap iron salt (FeCl2$4H2O) and tert-butylhydroperoxide (70% in water) as a stoichiometric oxidant is described. Control experiments indicated that this reaction might involve radical species. This method proved to be general, generating a family of 30 benzamides and was applied to the preparative synthesis of anti-anxiety drug moclobemide.

Oxyarylation and aminoarylation of styrenes using photoredox catalysis

A three-component coupling of styrenes is reported, using photoredox catalysis to achieve simultaneous arylation and C-O or C-N bond formation across the styrene double bond.

Carbon-carbon bond formations at the benzylic positions of N-benzylxanthone imines and N-benzyldi-1-naphthyl ketone imine

Two N-benzyl imines are designed to allow for carbon-carbon bond formations at the aminated benzylic positions. Direct benzylic arylation reactions of N-benzylxanthone imine with aryl chlorides proceed under palladium catalysis in the presence of cesium hydroxide, yielding the corresponding benzhydrylamine derivatives. Alkylation reactions of N-benzyldi-1-naphthyl ketone imine with alkyl halides in the presence of potassium tert-butoxide afford the corresponding 1-phenylalkylamines in high yields. Conjugate addition of N-benzyldi-1-naphthyl ketone imine is also described.

Solid-phase synthesis of β-Amino ketones and six-ring carbamates via immobilized α-alkoxycarbonylamino sulfones

(figure presented) β-Amino ketones and substituted 1,3-oxazinan-2-ones have been synthesized utilizing polymer-bound and carbamate-linked α-alkoxycarbonylamino sulfones. Key steps in the synthesis are the immobilization of the N-acylimine precursor, the Mannich-type addition of various nucleophiles, and the diastereoselective reduction of the resin-bound ketone.

Single Electron Transfer versus Nucleophilic Ring Opening in Reactions of Cis-Trans Pairs of Activated 2-Phenylaziridines. Strong Influence of Nitrogen Pyramid for N-Benzoylaziridines

Activated 2-phenylaziridines with a second substituent R in position 3 were made to react with xanthyl anion X(1-).Nucleophilic ring opening is the only reaction that occurs with sulfonyl activation.The analogous N-benzoylaziridines 1 undergo this type of ring opening when the two substituents Ph and R are trans.The cis isomers (cis-1, Ph and R cis) react in this manner to a negligible extent if any.The (nearly) exclusive ring cleavage reaction of cis-1 is C-N homolysis of an intermediate ketyl formed by single electron transfer (SET) from X(1-).This cis-trans phenomenon is in accordance with the hypothesis that the two competing reactions depend in an opposite manner on the steepness of the nitrogen pyramid.A predominant or exclusive final result of SET is reductive aziridine opening and dimerization of the xanthyl radical X(.).Formation of both diastereomers of the amidoethylated xanthene in one case (R = Me) is evidence for a cross combination of X(.) with the radical formed by homolytic ring opening.Cross combination is also a likely path for R = H (no cis-trans isomerism), in addition to reductive ring opening. cis-Aziridines with dimethylcarbamoyl on nitrogen do not react via SET since the ketyl is not stabilized and therefore difficult to generate.Carbonyl attack on both types of acylaziridines competes more or less successfully with the two ring cleavage reactions.

A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines

A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented.Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3.Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields.The method is also highly effective with (2-phenylethyl)amides.

Electron transfer reactions. Reaction of nitrogen heterocycles with potassium

The results of our studies on potassium-induced transformations of some selected nitrogen heterocycles are presented.The substrates under investigation include 2,3-diphenylindole (1a), 2,3-diphenyl-1-methylindole (1b), 1,2,3-triphenylindole (1c), 2,3,4,5-tetraphenylpyrrole (5a), 1,2,3,5-tetraphenylpyrrole (5b), 1-benzyl-2,3,5-triphenylpyrrole (5c), 2,4,5-triphenyloxazole (15a), 4,5-diphenyl-2-methyloxazole (15b), 2,4-diphenyl-5-methyloxazole (15c), and 2,4,5-triphenylimidazole (19).Treatment of 1a with potassium in THF gave 9H-dibenzocarbazole (3a), whereas 1c gave a mixture of 9-phenyl-9H-dibenzocarbazole (3c) and 2,3-diphenylindole (1a).Under identical conditions, 1b gave only the cleavage product 1a.In contrast, when the reactions of 1a,c were carried out with potassium in THF saturated with oxygen, and with potassium superoxide in benzene containing 18-crown-6, a mixture of 2-benzamidobenzophenone (4a), the carbazoles 3a,c, and 1a was formed.Although no product was isolated on treatment of 5a with potassium in THF, the reaction of 5a with potassium in THF saturated with oxygen gave a mixture of tetraphenylpyrazine (7a), the benzoylaminostilbene 8a, the lactam 12a, benzamide (11a), and benzoic acid (14).Similar results were obtained in the reaction of 5a with potassium superoxide.The reaction of N-substituted pyrroles such as 5b,c with potassium gave the NH pyrrole 9b in each case, whereas the reaction of 5b,c with potassium in THF, saturated with oxygen, gave a mixture of 9b, the butanone 10b, the 1,4-dione 13b, the lactam 12b, the amides 11a-c, and benzoic acid (14).Attempted reactions of 5b,c with potassium superoxide did not give any isolable product; most of the starting material could be recovered unchanged in each case.A mixture of N-(1,2-diphenylethyl)benzamide (18a) and benzoic acid (14) was formed in the reaction of the oxazole 15a with potassium, whereas 15b,c, under analogous conditions, gave the N-vinylamides 17b,c and benzoic acid (14).In contrast, treatment of the imidazole 19 with potassium in THF did not give any product; however, when the reaction of 19 was carried out with potassium in THF saturated with oxygen, and with potassium superoxide, dibenzamide (21) was isolated, in each case.Radical ions have been invoked as intermediates in the transformation of the different substrates to the observed products.Cyclic voltammetric studies have been carried out to measure the reduction potentials of these radical anion intermediates.These radical anions have also been generated by pulse radiolysis in methanol, and their absorption spectra recorded.

Evolutions differentes de radicaux anions formes par voie chimique ou electrochimique

Chemical and electrochemical reductions of N-aroylaziridines 1 are described and compared.The first step is a single electron transfer (1 +e -> 1-. -> 1'-.).But compounds obtained from 1'-. are depending on the method used way followed: chemical reduction of N-cinnamoylaziridine 1e provides pyrrolidone 10e; but oxazoline 11e is available by electrochemical reduction of the same starting material 1e.Counter ion seems responsible of these different results.In agreement with this hypothesis, it is shown that pyrrolidone 10e is obtained from 1j only in presence of a counter ion.