14155-36-3

Upstream product

• 873-49-4 cyclopropylbenzene 
• 4850-49-1 1-phenyl-1,3-propanediol 
• 936-59-4 3-chloropropiophenone 
• 18776-12-0 3-chloro-1-phenyl-propan-1-ol 
• 104-52-9 phenylpropyl chloride 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 7719-09-7 thionyl chloride 
• 772-00-9 4-phenyl-1,3-dioxane 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 56-23-5 tetrachloromethane 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 18776-12-0 3-chloro-1-phenyl-propan-1-ol 
• 4320-42-7 3-dimethylamino-1,1-diphenyl-propan-1-ol 
• 5554-65-4 1-(dimethylamino)-3-phenylpentan-3-ol 
• 36321-02-5 N,N-dimethyl-3-phenylpentan-1-amine 
• 55702-58-4 1-methyl-2-phenylazetidine 

Relevant academic research and scientific papers

Cu-Catalyzed Site-Selective Benzylic Chlorination Enabling Net C–H Coupling with Oxidatively Sensitive Nucleophiles

Site-selective chlorination of benzylic C–H bonds is achieved using a CuICl/bis(oxazoline) catalyst with N-fluorobenzenesulfonimide as the oxidant and KCl as a chloride source. This method exhibits higher benzylic selectivity, relative to estab

Diverse ring opening of thietanes and other cyclic sulfides: An electrophilic aryne activation approach

Organosulfides are a common class of structure units in bioactive molecules and functional materials motivating continuous developments of efficient synthetic methods. Herein, we report an electrophilic aryne-activated ring opening protocol of one or two

Azetidine-Borane Complexes: Synthesis, Reactivity, and Stereoselective Functionalization

The present study reports, for the first time, the synthesis and structural features of azetidine-borane complexes, as well as their reactivity in lithiation reactions. A temperature-dependent stereoselectivity has been disclosed in the reaction of borane with N-alkyl-2-arylazetidines, allowing for a stereoselective preparation of azetidine-borane complexes 2 and 3. A regioselective hydrogen/lithium permutation, at the benzylic position, was observed in lithiation reactions of complexes possessing a syn relationship, between the ring proton and the BH3 group. In contrast, scarce or no reactivity was noticed in complexes lacking such a stereochemical requirement. The configurational stability of the lithiated intermediates has also been investigated, in order to shed some light on the stereoselectivity of the lithiation/electrophile trapping sequence. Calculations helped in supporting experimental observations, concerning structure and reactivity of these azetidine-borane complexes. Data suggest that the BH3 group could promote the lithiation reaction likely by an electrostatic complex induced proximity effect. Interestingly, a new synthetic strategy for the synthesis of N-alkyl-2,2-disubstituted azetidines has been developed.

2-Arylazetidines as ligands for nicotinic acetylcholine receptors

Alternative and complementary procedures were adopted for preparing 2-arylazetidine derivatives in moderate to good yields. Preliminary biological evaluation of 2-arylazetidines as ligands of nicotinic acetylcholine receptors allowed to identify chloro-substituted analogs as the most interesting congeners. The title compounds may be considered as suitable hit compounds for developing new nicotinic acetylcholine receptor ligands that may be safer than the currently available drugs targeting nicotinic acetylcholine receptors. Our described synthetic approaches enable facile access to a large number of diversely decorated azetidines for studying the structure-activity relationships and for refining the toxico-pharmacological profile of these agents.

Desulfurative Chlorination of Alkyl Phenyl Sulfides

The chlorination of readily available secondary and tertiary alkyl phenyl sulfides using (dichloroiodo)benzene (PhICl2) is reported. This mild and rapid nucleophilic chlorination is extended to sulfa-Michael derived sulfides, affording elimination-sensitive β-chloro carbonyl and nitro compounds in good yields. The chlorination of enantioenriched benzylic sulfides to the corresponding inverted chlorides proceeds with high stereospecificity, thus providing a formal entry into enantioenriched chloro-Michael adducts. A mechanism implying the formation of a dichloro-λ4-sulfurane intermediate is proposed.

Synthesis of 3-Aryl-1-aminopropane Derivatives: Lithiation-Borylation-Ring-Opening of Azetidinium Ions

In situ generated 2-phenyl-azetidinium ylides react with boronic esters to form acyclic γ-dimethylamino tertiary boronic esters. The transformation is believed to involve the formation of a zwitterionic boronate, which subsequently undergoes ring-opening 1,2-migration, which is promoted by the relief of ring strain. Owing to the configurational instability of the initially formed ylides, which appear to be in equilibrium with the open-chain carbene form, the reaction is not stereospecific. The C-B bond of the γ-dimethylamino tertiary boronic esters can be transformed into a variety of functional groups (C-OH, C-vinyl, C-H, C-BF3), thus giving a diverse selection of 3-aryl-1-aminopropanes, which represent a privileged motif among drug molecules.

Chlorination of aliphatic primary alcohols via triphosgene-triethylamine activation

Activation of primary aliphatic alcohols with triphosgene and triethylamine mixtures afforded either alkyl chloride or diethylcarbamate products, and the switch in selectivity appeared to be driven by sterics. The reaction conditions to achieve this highly useful transformation were unexceptionally mild and readily tolerated by a wide range of sensitive functionalities.

Reactions of cyclopropanes with potassium dihaloiodates

Reactions of potassium dihaloiodates with arylcyclopropanes and polycyclic compounds containing a cyclopropane fragment characterized by different degrees of strain lead to formation of mixed 1,3-halogenation products. If iodohalogenation should give rise to products having a iodine atom in the benzylic position, 1,3-dichloro or 1,3-dibromo derivatives are formed. Iodohalogenation of exo-tricyclo[3.2.1.02,4]octane is stereoselective and is accompanied by Wagner-Meerwein rearrangement.

FREE RADICAL CHLORINATION AND ONE-ELECTRON OXIDATION OF ARYLCYCLOPROPANES. DESIGNER PROBES FOR CYTOCHROME P-450 HYDROXYLATION MECHANISMS

Arylcyclopropyl radicals can be formed under mild conditions (phase-transfer-catalyzed chlorination) and give rise to cyclopropyl products; in contrast one-electron oxidation of arylcyclopropanes by Mn(OAc)3 leads to fragmentation of the cyclopropane ring and the formation of acyclic products.