70197-10-3

Upstream product

• 98-82-8 Isopropylbenzene 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 591-50-4 iodobenzene 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 137595-22-3 N-(4-tolylsulfonyl)-2-methyl-2-phenylaziridine 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 70-55-3 toluene-4-sulfonamide 
• 98-80-6 phenylboronic acid 
• 24395-14-0 N-(p-tolylsulfonyl)-2-phenylaziridine 
• 75-24-1 trimethylaluminum 
• 917-54-4 methyllithium 
• 51136-87-9 tris(2-phenylpropyl)borane 

Relevant academic research and scientific papers

Catalytic Asymmetric [3 + 2] Annulation of Hantzsch Esters with Racemic N-Sulfonylaziridines

Hantzsch esters (HEs) served as two-carbon partners in a copper(I)-catalyzed enantioselective [3 + 2] annulation with racemic 2-(hetero)aryl-N-sulfonyl aziridines via kinetic resolution to provide pyrrolo[2,3-b]tetrahydropyridines containing multiple contiguous stereogenic centers including all-carbon quaternary centers in excellent yields and enantiopurities and moderate-to-excellent diastereoselectivities. Mainly dependent upon the structures of the aziridines, a competitive hydrogenolysis process with HEs as the hydrogen source was also observed in some cases.

Practical Intermolecular Hydroarylation of Diverse Alkenes via Reductive Heck Coupling

The hydroarylation of alkenes is an attractive approach to construct carbon-carbon (C-C) bonds from abundant and structurally diverse starting materials. Herein we report a palladium-catalyzed reductive Heck hydroarylation of aliphatic and heteroatom-substituted terminal alkenes and select internal alkenes with an array of (hetero)aryl iodides. The reaction is anti-Markovnikov selective with terminal alkenes and tolerates a wide variety of functional groups on both the alkene and (hetero)aryl coupling partners. Additionally, applications of this method to complex molecule diversifications are demonstrated. Mechanistic experiments are consistent with a mechanism in which the key alkylpalladium(II) intermediate is intercepted with formate and undergoes a decarboxylation/C-H reductive elimination cascade to afford the saturated product and turn over the cycle.

A novel rhodium-catalyzed domino-hydroformylation-reaction for the synthesis of sulphonamides

An efficient and highly selective method for the synthesis of sulphonamides by a domino hydroformylation-reductive sulphonamidation reaction has been developed. Various olefins and sulphonamides are converted into the desired products in good yields and with excellent selectivities in the presence of a rhodium/Naphos catalyst. This journal is

Regioselective rhodium(I)-catalyzed hydroarylation of protected allylic amines with arylboronic acids

A novel regioselective rhodium(I)-catalyzed hydroarylation of unactivated alkenes with arylboronic acids is described. The catalytic system employs [Rh(COD)OH]2 and BINAP to effect the addition of various arylboronic acids to protected allylic amines. The regioselectivity was found to be highly dependent on the protecting group, favoring the linear addition product with up to 92% yield and >20:1 regioselectivity.

A practical regioselective ring-opening of activated aziridines with organoalanes

The regioselective ring-opening of N-protected 2-phenylaziridines is accomplished by the addition of organoalanes in dichloromethane. With this simple method it is possible to introduce alkyl, alkenyl and alkynyl substituents at the benzylic position of t

Facile amine formation by intermolecular catalytic amidation of carbon-hydrogen bonds

A simple copper-based catalytic system has been developed for the carbon-hydrogen amidation reaction. The copper-homoscorpionate complex Tp Br3Cu(NCMe) catalyzes the transfer of the nitrene unit NTs (Ts = p-toluenesulfonyl) and its subsequent insertion into the sp3 C-H bonds of alkyl aromatic and cyclic ethers or the sp2 C-H bonds of benzene using PhI=NTs as the nitrene source, affording the corresponding trisubstitued NR1HTs amines in moderate to high yields. The use of the environmentally friendly chloramine-T has also proven effective, with the advantage that sodium chloride is formed as the only byproduct. A tandem, one-pot consecutive nitrene-carbene insertion system has been developed to yield amino acid derivatives.

Notable coordination effects of 2-pyridinesulfonamides leading to efficient aziridination and selective aziridine ring opening

(Chemical Equation Presented) We have developed, on the basis of a chelation-strategy, an efficient copper-catalyzed aziridination protocol with the use of 5-methyl-2-pyridinesulfonamide and Phl(OAc)2. The reaction proceeds smoothly under mild conditions to give aziridines in moderate to good yields in the absence of external ligands or bases. The coordination-assisted approach offers the additional benefits that efficient deprotection of the N-substituent and selective aziridine ring-opening are effectively achieved.

Reaction of [N-(p-toluenesulfonyl)imino]phenyliodinane with trialkylboranes: Transformation of a boron-carbon bond into a nitrogen-carbon bond

N-Toluenesulfonyl protected primary amines were obtained in good to excellent yield by reaction of [N-(p-toluenesulfonyl)imino]phenyliodinane with trialkylboranes.