33603-47-3

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 100-61-8 N-methylaniline 
• 86576-67-2 N-phenyl-N-methyl 3-pyrrolidinylpropenoamide 
• 4392-24-9 Cinnamyl bromide 
• 86576-68-3 N-phenyl-N-methyl 3-piperidinylpropenoamide 
• 86576-69-4 (E)-N-methyl-3-morpholino-N-phenylacrylamide 
• 50-00-0 formaldehyd 
• 92573-86-9 N-[(2E)-3-phenylprop-2-en-1-yl]aniline 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 673-32-5 1-Phenylprop-1-yne 
• 21040-45-9 Cinnamyl acetate 
• 14371-10-9 (E)-3-phenylpropenal 
• 2739-12-0 N-methylaniline hydrochloride 
• 104-54-1 3-Phenylpropenol 

Downstream Products

• 1310708-05-4 N-methyl-2-[(2E)-3-phenylprop-2-en-1-yl]aniline 
• 1310708-06-5 N-methyl-4-[(2E)-3-phenylprop-2-en-1-yl]aniline 
• 27623-83-2 1-methyl-4-phenyl-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

Aerobic Allylic Amination Catalyzed by a Pd(OAc)2/P(OPh)3System with Low Catalyst Loading

A Pd(OAc)2/P(OPh)3 combination catalyzed Tsuji-Trost-Type allylic amination under aerobic conditions. Both aromatic and aliphatic secondary amines were transformed into the corresponding allylic amines with a tiny amount of the catalyst system (typically 0.02 mol % Pd), only when allylic phosphates were employed as electrophiles. Other typical electrophiles, such as allylic acetate and carbonate, were marginally reactive. A Pd(0) complex, Pd[P(OPh)3]3, formed in situ was suggested as an active species by mechanistic experiments.

Practical regio- and stereoselective azidation and amination of terminal alkenes

There is significant interest in developing more rapid and efficient production of nitrogen-containing allylic compounds, as widely used in various syntheses. This work reports a variety of allylic azides and allylic amines synthesized by an efficient, new one-pot protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)-isomer, under metal-free conditions. This process tolerates several functional groups including halogen-containing molecules; it is general for azides and amine nucleophiles; and, adducts were obtained in good yields.

C-N Bond Formation from Allylic Alcohols via Cooperative Nickel and Titanium Catalysis

Amination of allylic alcohols is facilitated via cooperative catalysis. Catalytic Ti(O-i-Pr)4 is shown to dramatically increase the rate of nickel-catalyzed allylic amination, and mechanistic experiments confirm activation of the allylic alcohol by titanium. Aminations of primary and secondary allylic alcohols are demonstrated with a variety of amine nucleophiles. Diene-containing substrates also cyclize onto the nickel allyl intermediate prior to amination, generating carbocyclic amine products. This tandem process is only achieved under our cooperative catalytic system.

Direct Allylic Amination of Allylic Alcohol Catalyzed by Palladium Complex Bearing Phosphine-Borane Ligand

The direct electrophilic, nucleophilic, and amphiphilic allylations of allylic alcohol by use of a palladium catalyst and organometallic reagents such as organoborane and organozinc has been developed. The phosphine-borane compound works as the effective ligand for palladium-catalyzed direct allylic amination of allylic alcohol. Thus, with secondary amines, the reaction was completed in only 1 h, even at room temperature.

Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines

The hydroamination of internal alkynes via tandem rhodium catalysis gives branched N-allylic indolines with high regio- and enantioselectivity. An acid switch provides access to the linear isomer in preference to the branched isomer by an isomerization me

Photoredox α-vinylation of α-amino acids and N -aryl amines

A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.

Deammoniative condensation of primary allylic amines with nonallylic amines

An unprecedented deammoniative condensation reaction of primary allylic amines with nonallylic amines has been developed through C-N bond cleavage. In the presence of 5 mol% palladium diacetate, 10 mol% 1,4-bis(diphenylphosphino) butane (dppb), and 5 mol% p-toluenesulfonic acid (TsOH), a range of α-unbranched primary allylic amines smoothly underwent deammoniative condensation with nonallylic amines in an α-selective fashion to give structurally diverse secondary and tertiary amines in good to excellent yields and E selectivity. Replacing dppb with racemic 2,2-bis(diphenylphosphino)-1,1- binaphthyl (BINAP) permitted the deammoniative condensation of enantioenriched α-chiral primary allylic amines with nonallylic amines to proceed with complete retention of configuration. Electrospray ionization (ESI) mass spectrometric analysis of the reaction mixture permitted the identification of some π-allylpalladium intermediates, and plausible mechanisms have been proposed to account for the regioselectivity and stereospecificity of the deammoniative condensation reaction. A range of enantioenriched primary allylic amines underwent palladium/acid-catalyzed direct substitution with nonallylic amines in a stereospecific manner. Copyright

An efficient and convenient palladium catalyst system for the synthesis of amines from allylic alcohols

A novel catalyst system for efficient amination of allylic alcohols with aryl and alkyl amines is presented. By applying a convenient combination consisting of Pd(OAc)2/1,10-phenanthroline, a variety of allylic alcohols reacted smoothly to give the corresponding secondary and tertiary amines in good to excellent yields with high regioselectivity. The usefulness of our protocol is demonstrated in the one-step synthesis of the antifungal drug naftifine and the calcium channel blocker flunarizine. One pot is all it takes: By applying a convenient combination consisting of Pd(OAc)2/1,10- phenanthroline, a variety of allylic alcohols reacts smoothly to give the corresponding secondary and tertiary amines in good to excellent yields with high regioselectivity (see picture).

Simple and convenient approach for synthesis of tetrahydroquinoline derivatives and studies on aza-Cope rearrangement

A simple and novel synthesis of 1,2,3,4-tetrahydroquinoline derivatives by polyphosphoric acid-assisted reaction of N-aryl allyl anilines prepared from anilines has been reported. The generality and scope of the approach has been demonstrated by extending it to the synthesis of 1,2,5,6-tetrahydro-4H- pyrrolo[3,2,1-ij]quinoline (lilolidine) and 2,3,6,7-tetrahydro-1H,5H-pyrido[3,2, 1-ij]quinoline (julolidine). Further, Lewis acid- mediated aza-Cope rearrangement of various N-aryl allyl anilines has been demonstrated.

Surfactant-Enabled Transition Metal-Catalyzed Chemistry

In one embodiment, the present application discloses mixtures comprising (a) water in an amount of at least 1% wt/wt of the mixture; (b) a transition metal catalyst; and (c) one or more solubilizing agents; and methods for using such mixtures for performing transition metal mediated bond formation reactions.