66236-20-2

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 267002-56-2 4-chloro-2-(prop-2-en-1-yl)aniline 
• 13519-80-7 N-allyl-4-chloroaniline 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 1094359-15-5 5-chloro-2-(2,2,6,6-tetramethyl-piperidin-1-yloxymethyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole 
• 1251443-45-4 5-chloro-2-(iodomethyl)-1-(4-methylbenzene-1-sulfonyl)-2,3-dihydro-1H-indole 
• 1356133-29-3 (R)-2-(3,3-diphenylallyl)-5-chloro-1-tosylindoline 
• 1380538-78-2 (S)-5-chloro-2-(iodomethyl)-1-tosylindoline 
• 1609653-20-4 C₁₇H₁₅ClF₃NO₂S 

Relevant academic research and scientific papers

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.

Palladium-Catalyzed Fluoroalkylative Cyclization of Olefins

A palladium-catalyzed fluoroalkylative cyclization of olefins with readily available Rf-I reagents to afford the corresponding fluoroalkylated 2,3-dihydrobenzofuran and indolin derivatives with moderate to excellent yields is reported. This novel procedure provides an efficient method for the construction of Csp3-CF2 and C-O/N bonds in one step. A wide range of functional groups are tolerated. It is proposed that a radical/SET (single electron transfer) pathway proceeding via the fluoroalkyl radical may be involved in the catalytic cycle.

Palladium-Catalyzed Dehydrogenative Difunctionalization of Aminoalkenes with Aminals as Oxidants and Electrophiles

A novel palladium-catalyzed aminomethylamination of aminoalkenes with an aminal, functioning not only as an aminomethylation reagent but also as an oxidant, was developed. This direct and operationally simple protocol provides a fundamentally novel and unique approach toward the synthesis of 2-(2-aminoethyl)indoles and 2-(2-aminoethyl)pyrrolidines, which are important building blocks in synthetic organic chemistry. The unity of this method was highlighted by the rapid synthesis of Alosetron, a drug used for the treatment of irritable bowel syndrome.

Thioamination of Alkenes with Hypervalent Iodine Reagents

An efficient thioamination of alkenes mediated by iodine(III) reagents is described. The use of different sulfur nucleophiles allows the flexible synthesis of 1,2-aminothiols from alkenes. By employing chiral iodine(III) reagents, a stereoselective version of the thioamination protocol has also been developed.

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

M-CPBA-Mediated Intramolecular Aminohydroxylation of N-Sulfonyl Aminoalkenes to Synthesize β-Hydroxyl Cyclic Amines

A variety of structurally diverse N-sulfonyl-protected aminoalkenes readily reacted with m-CPBA to produce a series of β-hydroxyl cyclic amines in high yields through intramolecular aminohydroxylation. This metal-free and easy-to-handle synthetic methodol

Organocatalytic Stereoselective Iodoamination of Alkenes

A new chiral thiohydantoin catalyst is used for the stereoselective iodoamination of alkenes. N-iodosuccinimide as the source of the electrophilic iodine is activated by catalytic amounts of different additives which also influence the regioselectivity of some cyclizations.

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