99858-43-2

Upstream product

• 536-74-3 phenylacetylene 
• 118965-14-3 5-phenylpent-4-enenitrile 
• 13159-16-5 5-phenyl-4-penten-1-ol 
• 24595-58-2 5-phenylpent-4-yn-1-ol 
• 5390-04-5 pent-1-yn-5-ol 
• 591-50-4 iodobenzene 
• 13325-10-5 4-Aminobutanol 
• 3112-88-7 Benzyl phenyl sulfone 
• 127808-49-5 5-phenylpent-4-yn-1-amine 

Downstream Products

• 940909-11-5 (E)-4-methyl-N-(5-phenylpent-4-en-1-yl)benzenesulfonamide 
• 428453-40-1 N-(4-toluenesulfonyl)-(Z)-5-phenylpent-4-enylamine 
• 244016-01-1 trans-N-phenyl-5-phenyl-4-penten-1-amine 

Relevant academic research and scientific papers

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.).

Palladium-Catalyzed Aerobic Oxidative Cyclization of Aliphatic Alkenyl Amides for the Construction of Pyrrolizidine and Indolizidine Derivatives

An efficient palladium-catalyzed aerobic oxidative cyclization has been developed to synthesize a variety of pyrrolizidine and indolizidine derivatives from simple aliphatic alkenyl amides in moderate to good yields. The reaction features the capability of accessing various N-heterocycles and the use of molecular oxygen (1 atm) as the green oxidant.

Direct Olefination of Alcohols with Sulfones by Using Heterogeneous Platinum Catalysts

Carbon-supported Pt nanoparticles (Pt/C) were found to be effective heterogeneous catalysts for the direct Julia olefination of alcohols in the presence of sulfones and KOtBu under oxidant-free conditions. Primary alcohols, including aryl, aliphatic, allyl, and heterocyclic alcohols, underwent olefination with dimethyl sulfone and aryl alkyl sulfones to give terminal and internal olefins, respectively. Secondary alcohols underwent methylenation with dimethyl sulfone. Under 2.5 bar H2, the same reaction system was effective for the transformation of alcohol OH groups to alkyl groups. Structural and mechanistic studies of the terminal olefination system suggested that Pt0 sites on the Pt metal particles are responsible for the rate-limiting dehydrogenation of alcohols and that KOtBu may deprotonate the sulfone reagent. The Pt/C catalyst was reusable after the olefination, and this method showed a higher turnover number (TON) and a wider substrate scope than previously reported methods, which demonstrates the high catalytic efficiency of the present method. Olefination of alcohols: The first heterogeneous catalytic terminal and internal olefination of primary alcohols and methylenation of secondary alcohols with sulfones, a reusable carbon-supported Pt catalyst, and KOtBu is reported (see scheme).