244016-01-1

Upstream product

• 28131-24-0 tert-butyl N-methyl-N-(phenyl)carbamate 
• 103-72-0 phenyl isothiocyanate 
• 591-50-4 iodobenzene 
• 99858-43-2 5-phenylpent-4-enylamine 
• 118965-14-3 5-phenylpent-4-enenitrile 
• 536-74-3 phenylacetylene 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 33599-84-7 methyl (E)-5-phenyl-4-pentenoate 
• 119793-72-5 (E)-2-(3-phenyl-allyl) malonic acid dimethyl ester 
• 3422-01-3 tert-butyl phenylcarbamate 
• 62-53-3 aniline 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 100-61-8 N-methylaniline 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 72709-30-9 N-phenyl-2-phenylpiperidine 

Relevant academic research and scientific papers

Titanium-catalyzed intermolecular hydroaminoalkylation of conjugated dienes

Ti me kangaroo down: Conjugated dienes undergo intermolecular hydroaminoalkylation in the presence of Ti catalyst [Ind2TiMe 2] (Ind=η5-indenyl). This new reaction offers a highly atom-efficient approach to homoallylic amines from 1,3-butadienes. Copyright

Olefin Oxyamination with Unfunctionalized N-Alkylanilines

N-Alkylanilines have rarely been used in oxyamination reactions, due to the normally necessary pre-functionalization of the N-atom. Also, the formation of aminium radical cations (ARCs) of anilines bearing alkyl substituents is plagued by the ARC's tendency to instantaneously convert to α-amino radicals or iminium ions. We present a readily available reagent combination that addresses both challenges, and thus allows for an oxyamination with N-alkylanilines via ARCs as the crucial reactive intermediates and excellent diastereoselectivity. (Figure presented.).

Lewis Base-Boryl Radicals Enabled the Desulfurizative Reduction and Annulation of Thioamides

A new protocol for radical transformations of thioamides promoted by Lewis base-boryl radicals is reported. The desulfurizative reduction to access organic amines was enabled utilizing 4-dimethylaminopyridine-BH3 as the boryl radical precursor and PhSH as the polarity reversal catalyst. Alternatively, the chain process for unsaturated thioamides was switched to an annulation reaction using N-heterocyclic carbene-BH3 as the boryl radical precursor and sterically bulky Ph3CSH as the catalyst, allowing for the construction of N-heterocyclic and carbocyclic skeletons.

A 2,6-bis(phenylamino)pyridinato titanium catalyst for the highly regioselective hydroaminoalkylation of styrenes and 1,3-butadienes

The C-C bond forming catalytic hydroaminoalkylation of terminal alkenes, 1,3-dienes, or styrenes allows a direct and highly atom efficient (100 %) synthesis of amines which can result in the formation of two regioisomers, the linear and the branched product. We present a new titanium catalyst with 2,6-bis(phenylamino)pyridinato ligands for intermolecular hydroaminoalkylation reactions of styrenes and 1-phenyl-1,3-butadienes that delivers the corresponding linear hydroaminoalkylation products with excellent regioselectivities. Linear progress: A new Ti complex with 2,6-bis(phenylamino) pyridinato ligands catalyzes highly regioselective hydroaminoalkylation reactions of styrenes. The process that directly gives access to the corresponding linear hydroaminoalkylation products offers a new and flexible synthetic approach towards pharmaceutically important 3-arylpropylamines. It is also possible to convert (E)-1-phenyl-1,3-butadienes into the corresponding linear products.

Catalytic olefin hydroamination with aminium radical cations: A photoredox method for direct C-N bond formation

While olefin amination with aminium radical cations is a classical method for C-N bond formation, catalytic variants that utilize simple 2° amine precursors remain largely undeveloped. Herein we report a new visible-light photoredox protocol for the intramolecular anti-Markovnikov hydroamination of aryl olefins that proceeds through catalytically generated aminium radical intermediates. Mechanistic studies are consistent with a process involving amine oxidation via electron transfer, turnover-limiting C-N bond formation, and a second electron transfer step to reduce a carbon-centered radical, rendering the overall process redox-neutral. A range of structurally diverse N-aryl heterocycles can be prepared in good to excellent yields under conditions significantly milder than those required by conventional aminium-based protocols.

Formation and behavior of intramolecular N-(styrylalkyl)aniline exciplexes

The photophysical and photochemical behavior of several aniline spacer - styrene molecules in which the spacer is a short polymethylene chain has been investigated. Long wavelength excitation selectively excites the aniline chromophore which undergoes intramolecular quenching by the styrene to yield an intramolecular exciplex. Exciplex fluorescence is observed for both of the tertiary anilines investigated and for one of the three secondary anilines. More rapid exciplex formation in nonpolar vs. polar solvents is attributed to the necessity of desolvating the polar aniline singlet in polar solvents. Intramolecular adduct formation is the major photochemical process for the secondary anilines, but is highly inefficient for the tertiary anilines. The behavior of the intramolecular aniline-styrene exciplexes is compared to that of the styrene-amine exciplexes previously investigated in this laboratory.