81097-20-3

Upstream product

• 59816-88-5 (2-allylphenyl)methanamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 24850-33-7 allyltributylstanane 
• 328088-13-7 N-(2-bromobenzyl)-4-methylbenzenesulfonamide 
• 3959-05-5 2-bromobenzylamine 
• 195624-82-9 ((2-bromobenzyl)oxy)triisopropylsilane 
• 84801-07-0 2-(prop-2-enyl)benzyl alcohol 
• 70-55-3 toluene-4-sulfonamide 
• 18982-54-2 o-bromobenzyl alcohol 

Downstream Products

• 81097-21-4 N-tosyl-3-methyl-1,2-dihydroisoquinoline 
• 1245741-93-8 C₂₃H₂₃NO₂S 
• 1380538-96-4 (3S)-3-(iodomethyl)-2-[(4-methylphenyl)sulphonyl]-1,2,3,4-tetrahydroisoquinoline 
• 1356133-47-5 (R)-3-(3,3-diphenylallyl)-2-tosyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Synthesis of Tetrahydroisoquinolines through an Iron-Catalyzed Cascade: Tandem Alcohol Substitution and Hydroamination

Rapid assembly of saturated nitrogen heterocycles - the synthetically more challenging variants of their aromatic relatives - can expedite the synthesis of biologically relevant molecules. Starting from a benzylic alcohol tethered to an unactivated alkene, an iron-catalyzed tandem alcohol substitution and hydroamination provides access to tetrahydroisoquinolines in a single synthetic step. Using a mild iron-based catalyst, the combination of these operations forms two carbon-nitrogen bonds and provides a unique annulation strategy to access this valuable core.

Copper-catalyzed enantioselective intramolecular alkene amination/intermolecular heck-type coupling cascade

Enantioselective copper-catalyzed cyclization of γ- alkenylsulfonamides and a δ-alkenylsulfonamide in the presence of a range of vinyl arenes results in variously functionalized 2-substituted chiral nitrogen heterocycles via a formal alkene C-H functionalization process. Application of this reaction to the concise synthesis of a 5-HT7 receptor antagonist is demonstrated.

Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer

Problem solved: The title reaction was used for the synthesis of chiral 2-bromo, chloro, and iodomethyl indolines and 2-iodomethyl pyrrolidines (see scheme). Stereocenter formation is believed to occur by enantioselective cis aminocupration and C-X bond formation is believed to occur by atom transfer. The ultility of the products as versatile synthetic intermediates was demonstrated, as was a radical cascade cyclization sequence. Copyright

Gold-catalyzed intramolecular aminoarylation of alkenes: C-C bond formation through bimolecular reductive elimination

(Chemical equation presented) Gold-ilocks and the 3 mol% catalyst: Bimetallic gold bromides allow the room temperature aminoarylation of unactivated terminal olefins with aryl boronic acids using Selectfluor as an oxidant. A catalytic cycle involving gold (I)/gold(III) and a bimolecular reductive elimination for the key C-C bond-forming step is proposed, dppm= bis(diphenylphosphanyl) methane.

Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes

The enantioselective oxidative cyclizations of γ-alkenyl arylsulfonamides and a δ-alkenyl arylsulfonamide for the synthesis of nitrogen heterocycles are presented. The reactions are catalyzed by chiral copper(II) complexes, and MnO2 is used as

Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: Diastereoselectivity and mechanism

(Chemical Equation Presented) An expanded substrate scope and in-depth analysis of the reaction mechanism of the copper(II) carboxylate-promoted intramolecular carboamination of unactivated alkenes is described. This method provides access to N-functionalized pyrrolidines and piperidines. Both aromatic and aliphatic γ- and δ-alkenyl N-arylsulfonamides undergo the oxidative cyclization reaction efficiently. N-Benzoyl-2-allylaniline also underwent the oxidative cyclization. The terminal olefin substrates examined were more reactive than those with internal olefins, and the latter terminated in elimination rather than carbon-carbon bond formation. The efficiency of the reaction was enhanced by the use of more organic soluble copper(II) carboxylate salts, copper(II) neodecanoate in particular. The reaction times were reduced by the use of microwave heating. High levels of diastereoselectivity were observed in the synthesis of 2,5-disubstituted pyrrolidines, wherein the cis substitution pattern predominates. The mechanism of the reaction is discussed in the context of the observed reactivity and in comparison to analogous reactions promoted by other reagents and conditions. Our evidence supports a mechanism wherein the N-C bond is formed via intramolecular syn aminocupration and the C-C bond is formed via intramolecular addition of a primary carbon radical to an aromatic ring.

Palladium-Catalyzed Cyclization of ω-Olefinic Tosamides. Synthesis of Nonaromatic Nitrogen Heterocycles

The cyclization of aliphatic amino olefins to nonaromatic nitrogen heterocycles nas been accomplished by conversion of the amine to the corresponding p-toluenesulfonamide, followed by Pd(II)-catalyzed intramolecular amination of the olefin.The resulting t