830-41-1

Usage

InChI:InChI=1/C9H10BrNO2S/c1-2-7-11-14(12,13)9-5-3-8(10)4-6-9/h2-6,11H,1,7H2

Upstream product

• 107-11-9 1-amino-2-propene 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 701-34-8 4-bromo-benzenesulfonic acid amide 
• 934986-62-6 C₁₂H₆BrCl₃O₃S 
• 106-95-6 allyl bromide 
• 1950-71-6 4-bromobenzene-1-sulfonyl bromide 

Downstream Products

• 403793-16-8 N-allyl-4-iodobenzenesulfonamide 
• 851461-00-2 dithiocarbonic acid S-{1-[(4-bromobenzenesulfonylamino)methyl]-4-oxo-4-piperidin-1-yl-butyl} ester O-ethyl ester 
• 948913-37-9 4-bromo-N-oxiranylmethyl-N-prop-2-ynyl-benzenesulfonamide 
• 851461-08-0 dithiocarbonic acid S-(1-{[acetyl(4-bromobenzenesulfonyl)amino]methyl}-4-oxo-4-piperidin-1-yl-butyl) ester O-ethyl ester 
• 1208004-11-8 4-bromo-N-(2-fluoro-propyl)-benzenesulfonamide 
• 1208004-00-5 6-bromo-4-methyl-3,4-dihydro-2H-benzo[1,2]thiazine 1,1-dioxide 
• 1356020-07-9 C₂₂H₂₈BrNO₂S 
• 1356020-06-8 C₁₉H₂₄BrNO₂S 
• 1443931-50-7 9-allyl-1-(4-bromophenylsulfonyl)-6-methyl-2,3-dihydro-1H-benzo[f]indole 
• 1242104-94-4 C₁₀H₁₃BrFNO₂S 
• 1242104-68-2 N-(2-fluoropropyl)-N-methyl-4-octylaminobenzenesulfonamide 
• 1433140-36-3 3-(4-bromophenylsulfonyl)-1-phenyl-3-aza-bicyclo[3.1.0]hexan-2-one 
• 1379536-79-4 N-allyl-4-bromo-N-(phenylethynyl)benzenesulfonamide 
• 1647100-77-3 (E)-N-allyl-4-bromo-N-(4-methylpenta-2,4-dien-1-yl)benzenesulfonamide 

Relevant academic research and scientific papers

Twofold Radical-Based Synthesis of N, C-Difunctionalized Bicyclo[1.1.1]pentanes

Bicyclo[1.1.1]pentylamines (BCPAs) are of growing importance to the pharmaceutical industry as sp3-rich bioisosteres of anilines and N-tert-butyl groups. Here we report a facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy. Sulfonamidyl radicals, generated through fragmentation of α-iodoaziridines, undergo initial addition to [1.1.1]propellane to afford iodo-BCPAs; the newly formed C-I bond in these products is then functionalized via a silyl-mediated Giese reaction. This chemistry also translates smoothly to 1,3-disubstituted iodo-BCPs. A wide variety of radical acceptors and iodo-BCPAs are accommodated, providing straightforward access to an array of valuable aniline-like isosteres.

Copper(I)-Catalyzed Enyne Oxidation/Cyclopropanation: Divergent and Enantioselective Synthesis of Cyclopropanes

An efficient copper(I)-catalyzed enyne oxidation/cyclopropanation for the modular synthesis of cyclopropane derivatives is described, which represents the first non-noble metal-catalyzed enynes oxidation/cyclopropanation by the in situ generated α-oxo copper carbenes. This protocol allows the assembly of valuable cyclopropane-γ-lactams in generally good to excellent yields with excellent diastereoselectivity. More significantly, the enantioselective version of enyne oxidation/cyclopropanation has been disclosed with chiral copper catalysts.

Harnessing Energy-Transfer in N-Centered Radical-Mediated Synthesis of Pyrrolidines

Atom transfer radical addition (ATRA), cyclization (ATRC), and polymerization (ATRP) are valuable synthetic methods for the functionalization of olefins. With the advent of photoredox catalysis, visible-light became a popular tool for the initiation of these reactions. We have developed a protocol that enables easy access to distally functionalized pyrrolidines employing blue-light mediated atom transfer radical [3+2] cyclization. The reaction is scalable, proceeds at very mild conditions. tolerates various functional groups, and provides the corresponding products in good to excellent yields. If rigid olefins are utilized as the reaction partners, the products can be isolated as single diastereomers. The mechanistic investigations provide strong support for an energy-transfer mechanism.

Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles

A unique 1,7-S- and Se-shift reaction under Pummerer reaction conditions of 4-alkenyl-3-sulfinyl- and seleninylpyrroles was described. The usual Pummerer reaction of 4-(alkenylaminomethyl)-3-phenylsulfinylpyrroles and a successive reaction with tetrabutyl

Synthesis of 3-aza-bicyclo[3.1.0]hexan-2-one derivatives via gold-catalyzed oxidative cyclopropanation of N -allylynamides

N-Allylynamides with various functional groups and different substitution patterns can be converted into 3-aza-bicyclo[3.1.0]hexan-2-one derivatives in moderate to high yield using IMesAuCl/AgBF4 as the catalyst and pyridine N-oxide as the oxidant. A noncarbene mediated approach is proposed as the mechanism.

Trichlorophenol (TCP) sulfonate esters: A selective alternative to pentafluorophenol (PFP) esters and sulfonyl chlorides for the preparation of sulfonamides

2,4,6-Trichlorophenol (TCP) sulfonate esters undergo effective aminolysis under conventional heating and microwave irradiation; the reactivity of these species is such that chemoselective transformations of PFP sulfonate esters can be achieved. The Royal Society of Chemistry.

Gold(l)-catalyzed cascade cyclization reaction: Highly regio- and diastereoselective intermodular addition of water and alcohols to epoxy alkynes

We have developed a novel access to ketal skeletons through a highly regio- and diastereoselective intermolecular addition of water and alcohols to alkynyl epoxides catalyzed by goid(l). This procedure involves a domino three-membered ring-opening, 6-exo-

Synthesis of 3-arylpiperidines by a radical 1,4-aryl migration

(Chemical Equation Presented) A route to 3-arylpiperidines, 3-arylpyridines, and 5-arylpiperidin-2-ones involving a radical 1,4-aryl migration has been explored. The sequence requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with dilauroyl peroxide to give the 1,4-aryl transfer product, which upon acidic hydrolysis affords the desired piperidine derivative.

COPPER-CATALYZED FORMATION OF CARBON-HETEROATOM AND CARBON-CARBON BONDS

One aspect of the present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-sulfur bond between the sulfur atom of a thiol moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper(II)-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-carbon bond between the carbon atom of cyanide ion and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In another embodiment, the present invention relates to a copper-catalyzed method of transforming and aryl, heteroaryl, or vinyl iodide. Yet another embodiment of the present invention relates to a tandem method, which may be practiced in a single reaction vessel, wherein the first step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl iodide from the corresponding aryl, heteroaryl, or vinyl chloride or bromide; and the second step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl nitrile, amide or sulfide from the aryl, heteroaryl, or vinyl iodide formed in the first step.

Copper-catalyzed halogen exchange in aryl halides: An aromatic finkelstein reaction

A mild and general method for the conversion of aryl, heteroaryl, and vinyl bromides into the corresponding iodides was developed utilizing a catalyst system comprising 5 mol % of Cul and 10 mol % of a 1,2- or 1,3-diamine ligand. A variety of polar functional groups are tolerated, and even N-H containing substrates such as sulfonamides, amides, and indoles are compatible with the reaction conditions. Both the reaction rate and the equilibrium conversion of the aryl bromide depend on the choice of the halide salt and the solvent. The best results were obtained using Nal as the halide salt and dioxane, n-butanol, or n-pentanol as the solvents. Copyright