108714-94-9

Upstream product

• 32704-22-6 2-allyl-phenylamine 
• 98-09-9 benzenesulfonyl chloride 
• 62-53-3 aniline 
• 589-09-3 N-allyl-N-phenylamine 

Downstream Products

• 1356133-22-6 (R)-2-(3,3-diphenylallyl)-1-(phenylsulfonyl)indoline 
• 1609653-23-7 C₁₆H₁₄F₃NO₂S 
• 80360-21-0 1-(benzenesulfonyl)-2-methyl-1H-indole 

Relevant academic research and scientific papers

Synthesis of Benzofuran and Indole Derivatives Catalyzed by Palladium on Carbon

Benzofurans and indoles are key moieties in many natural products and pharmaceuticals. Herein, we describe a cheap and easy-to-execute strategy for the synthesis of benzofurans and indoles, employing Pd/C as the promoter. A variety of substituted allyl-anilines and allyl-phenols were converted into the desired products in good to excellent yields. Recycling of Pd/C was possible up to five cycles, keeping similar levels of reactivity.

Green Organocatalytic Synthesis of Indolines and Pyrrolidines from Alkenes

Employing a green and efficient 2,2,2-trifluoroacetophenone-catalyzed oxidation of alkenes, which utilizes H2O2 as the green oxidant, a novel and sustainable synthesis of indolines and pyrrolidines was developed. This constitutes a cheap, general and environmentally-friendly protocol for the synthesis of substituted nitrogen-containing heterocycles. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated leading to the desired nitrogen heterocycles in good to excellent yields. (Figure presented.).

Enantioselective Synthesis of 2-Bromomethyl Indolines via BINAP(S)-Catalyzed Bromoaminocyclization of Allyl Aniline

An enantioselective bromoamination of allyl aniline with N-bromosuccinimide (NBS) catalyzed by BINAP(S) (BINAP monosulfide) is described. This protocol could provide a range of chiral 2-bromomethyl indolines in good to excellent yields with up to 87% ee.

Copper-catalyzed radical cascade cyclization for the synthesis of phosphorated indolines

A novel and convenient approach to the synthesis of various phosphorated indolines via a copper-catalyzed radical cascade cyclization reaction has been developed. The reaction employs cheap copper as the catalyst and K2S2O8 as the oxidant under mild conditions. Various alkenes and P-radical precursors are compatible with this transformation. Preliminary mechanistic studies reveal that the addition of the P-radical may initiate the reaction, and then oxidative cyclization may be achieved to afford the desired product. This journal is

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.

Hg(OTf)2-BINAPHANE-catalyzed enantioselective anilino sulfonamide allyl alcohol cyclization

Chiral ligands: Hg(OTf)2-catalyzed cyclization of anilino sulfonamide allyl alcohol is described; this reaction gives 2-vinyl indoline derivatives in good yields and excellent enantioselectivity by using a chiral BINAPHANE ligand (see scheme).