106027-38-7

Upstream product

• 201230-82-2 carbon monoxide 
• 22774-81-8 N-(2-methylallyl)aniline 
• 1604-11-1 (S)-dimethyl 2-methylsuccinate 
• 62-53-3 aniline 
• 22644-27-5 (R)-methylsuccinic acid dimethyl ester 
• 21307-96-0 methyl 2-methylsuccinate 
• 100-61-8 N-methylaniline 

Relevant academic research and scientific papers

Copper-Catalyzed Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling

We present a strategy that difunctionalizes unactivated olefins in 1,2-positions with two carbon-based entities. This method utilizes alkyl/arylzinc reagents derived from olefin-tethered alkyl/aryl halides that undergo radical cyclization to generate C(sp3)-Cu complexes in situ, which are intercepted with aryl and heteroaryl iodides. A variety of (arylmethyl)carbo- and heterocycles (N, O) can be synthesized with this new method.

Nickel-catalyzed reductive cyclization of alkyl dihalides

The reductive coupling protocol to intramolecular cyclization of dihaloalkanes is presented. It leads to five- and six-membered rings, with the former being more efficient. The incorporation of secondary alkyl halides generally promotes coupling efficiency. To the best of our knowledge, this is the first catalytic ring-closure reaction arising from dihaloalkanes under chemical reductive conditions.

New method for the preparation of an active manganese species and its use for radical cyclization reactions

Reduction of Li2MnCl4 with magnesium in THF afforded a fairly active manganese species which readily initiated radical cyclization of 2-iodoethanal allylic acetals at room temperature. The corresponding 2-bromoethanal acetals also pr

A new route to N-aromatic heterocycles from the hydrogenation of diesters in the presence of anilines

The hydrogenation of dicarboxylic acids and their esters in the presence of anilines provides a new synthesis of heterocycles. [Ru(acac)3] and 1,1,1-tris(diphenylphosphinomethyl)ethane (triphos) gave good to excellent yields of the cyclic amines at 220 °C. When aqueous ammonia was used with dimethyl 1,6-hexadienoic acid, ?-caprolactam was obtained in good yield. A side reaction involving alkylation of the amine by methanol was suppressed by using diesters derived from longer chain and branched alcohols. Hydrogenation of optically pure diesters (dimethyl (R)-2-methylbutanedioate and dimethyl (S)-2-methylbutanedioate) with aniline afforded racemic 3-methyl-1-phenylpyrrolidine in 78% yield.

Tantalum catalyzed hydroaminoalkylation for the synthesis of α- And β-substituted N-heterocycles

Unprotected secondary amines are directly alkylated by C-H functionalization adjacent to nitrogen, thereby opening new routes toward the synthesis of α- and β-alkylated N-heterocycles. α-Alkylated piperidine, piperazine, and azepane products are prepared from heterocycles and alkenes in an atom-economic reaction with excellent regio- and diastereoselectivity. β-Alkylated N-heterocycles are synthesized via a scalable one-pot alkylation/cyclization procedure generating 3-methylated azetidines, pyrrolidines, and piperidines.

A new strategy for the preparation of an active Mn(0) and its use for radical cyclization reactions

Reduction of Li2-MnCl4 with magnesium in THF afforded a fairly active manganese species which readily initiated radical cyclization of 2- iodoethanal allylic acetals at room temperature. The corresponding 2- bromoethanal acetals also provided the same cyclized products upon treatment with the activated manganese reagent at reflux in THF. This reagent can also be used to induce tandem radical cyclizations, and the 5-exo/6-endo and 5- exo/6-exo modes are both available to give the products with trans- stereochemistry with regard to ring-junction. Further, the intramolecular type of sequential generation and utilization of radical and anionic species with this reagent have also been studied.

Synthesis of Pyrrolidines and Pyrrolidinones by the Rhodium Complex Catalyzed Cyclization of Unsaturated Amines

N-Allylic arylamines react with carbon monoxide, sodium borohydride, 2-propanol, and catalytic amounts of the zwitterionic complex η6-C6H6BPh3-Rh(COD)+ (1), to form pyrrolidines as the main products in most cases.Pyrrolidinones result from N-allylic alkylamines.An alternate route to the lactams from N-allylic alkylamines involves synthesis gas instead of CO/NaBH4, together with the dual catalytic system 1/2.Complementary to the N-allylic arylamine route to pyrrolidines with NaBH4 and 1 is the use of synthesis gas, 1, and 1,4-bis(diphenylphosphino)butane.