13314-74-4

Upstream product

• 33930-10-8 4-(1-(4-(dimethylamino)phenyl)cyclohexyl)-N,N-dimethylaniline 
• 108-94-1 cyclohexanone 
• 121-69-7 N,N-dimethyl-aniline 
• 67-64-1 acetone 
• 7647-01-0 hydrogenchloride 
• 13299-39-3 1-[4-(dimethylamino)phenyl]cyclohexanol 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 7570-92-5 cyclohexyl phenyl sulphide 
• 7353-91-5 4-dimethylaminophenylmagnesium bromide 
• 930-66-5 1-chlorocyclohexene 
• 22718-22-5 cyclohex-1-en-1-yl dimethylcarbamate 

Downstream Products

• 13299-39-3 1-[4-(dimethylamino)phenyl]cyclohexanol 

Relevant academic research and scientific papers

Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2

Herein, direct unreactive C-N borylation of aromatic amines by a photocatalyst was achieved. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B2pin2) proceeded using a pyrene catalyst under light irradiation to afford desired borylated products and aminoborane as a byproduct. The yield of the borylated product improved under a CO2 atmosphere which probably reduced the inhibitory effect of aminoborane. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.

Electro-Olefination—A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes

Conventional methods carrying out C(sp2)?C(sp2) bond formations are typically mediated by transition-metal-based catalysts. Herein, we conceptualize a complementary avenue to access such bonds by exploiting the potential of electrochemistry in combination with organoboron chemistry. We demonstrate a transition metal catalyst-free electrocoupling between (hetero)aryls and alkenes through readily available alkenyl-tri(hetero)aryl borate salts (ATBs) in a stereoconvergent fashion. This unprecedented transformation was investigated theoretically and experimentally and led to a library of functionalized alkenes. The concept was then carried further and applied to the synthesis of the natural product pinosylvin and the derivatization of the steroidal dehydroepiandrosterone (DHEA) scaffold.

Pd-catalyzed cross-coupling of highly sterically congested enol carbamates with grignard reagents via c-o bond activation

The palladium-catalyzed cross-coupling reaction of enol carbamates to construct highly sterically congested alkenyl compounds is presented for the first time. This protocol demonstrates the potential of using thermally stable and highly atom-economic enol electrophiles as building blocks in bulky alkene synthesis. This reaction accommodates a broad substrate scope with excellent Z/E isomer ratios, which also provides a new synthetic pathway for accessing Tamoxifen.

Iodine-catalyzed cycloalkenylation of dihydroquinolines and arylamines through a reaction with cyclic ketones under neat conditions

An iodine-catalyzed direct cycloalkenylation of dihydroquinolines and arylamines has been developed. This method consists of a Friedel-Crafts reaction between dihydroquinolines (or arylamines) and cyclic ketones in which the double bond is selectively generated throughout the course of the reaction resulting in a direct cycloalkenylation, under neat conditions.

Amido pincer nickel catalyzed kumada cross-coupling of aryl, heteroaryl, and vinyl chlorides

Amido pincer nickel complexes {Ni(Cl)[2-P(Ph2)C 6H4NC(Ph)=NAr]} (Ar = 4-MeC6H4, 1; Ar = 4-ClC6H4, 2; Ar = 4-MeOC6H4, 3) were shown to efficiently catalyze the cross-coupling of activated, unactivated, and deactivated aryl chlorides, N-heteroaryl chlorides, 1,4-dichlorobenzene, and vinyl chlorides with aryl Grignard reagents. Georg Thieme Verlag Stuttgart, New York.

Nickel-catalyzed alkenylative cross-coupling reaction of alkyl sulfides

A novel cross-coupling reaction of alkyl aryl sulfides with aryl Grignard reagents has been achieved to produce the alkenyl-aryl coupling products in high yields by using catalytic Ni(cod)2 and a bulky N-heterocyclic carbene ligand, SIPr.

Photoinduced charge separation in cyclohexylidene-based donor - (σ-bridge) - acceptor compounds - Building blocks for materials

We describe the syntheses and properties of five semi-rigid donor - (σ-bridge) - acceptor (D-σ-A) compounds. These compounds, which are candidates for incorporation in materials, have aniline-type donors and (mixed) cyano- and alkoxycarbonyl-1,1-difunctio