243671-17-2

Upstream product

• 36971-15-0 3-isopropyl-2-methyl-hex-5-en-3-ol 
• 75159-10-3 (E)-N-4-methylbenzylidene-4-toluenesulfonamide 
• 75159-10-3 N-(4-methylbenzylidene)-p-toluenesulfonamide 
• 106-95-6 allyl bromide 
• 106-42-3 para-xylene 
• 18925-10-5 allylzinc bromide 
• 70-55-3 toluene-4-sulfonamide 
• 589-18-4 4-Methylbenzyl alcohol 
• 104-87-0 4-methyl-benzaldehyde 
• 24850-33-7 allyltributylstanane 
• 762-72-1 allyl-trimethyl-silane 
• 188564-49-0 N-[(benzotriazol-1-yl)-p-tolylmethyl]-p-toluenesulfonamide 
• 24400-84-8 allyl triisopropylsilane 

Downstream Products

• 75159-10-3 N-(4-methylbenzylidene)-p-toluenesulfonamide 

Relevant academic research and scientific papers

Lewis acid-mediated [3+2] cycloaddition of allyltriisopropylsilane to N-sulfonyl aldimines

BF3·OEt2-mediated [3+2] cycloaddition of allyltriisopropylsilane to N-sulfonyl aldimine afforded silyl substituted pyrrolidines in good yields. Excellent cis selectivity was observed with aromatic aldimines.

Active bismuth mediated allylation of carbonyls/N-tosyl aldimines and propargylation of aldehydes in water

Abstract: Active bismuth is synthesized by the chemical reduction of bismuth trichloride using freshly prepared sodium stannite solution as the reducing agent at room temperature. The as-synthesized active bismuth is applied as a reagent for the synthesis of homoallyl alcohol/homopropargyl alcohol from allyl bromide/propargyl bromide and carbonyl compounds in water at 50°C. The homoallyl amines are also synthesized from N-tosyl aldimines and allyl bromide using active bismuth reagent in good yields. No assistance of organic co-solvent, co-reagent, phase transfer catalyst or inert atmosphere is required for this reaction. The waste bismuth material obtained after the completion of the organic reaction can be reduced to active bismuth by sodium stannite solution and successfully reused for mediating the allylation of aldehydes. Graphical Abstract:: Synopsis Active bismuth mediated allylation/crotylation of aldehydes is developed in water to get homoallyl alcohols. The method is also applied for the allylation of N-tosyl aldimines and propargylation of aldehydes in water to achieve the homoallyl amines and homopropargyl alcohols, respectively. The reactions do not require the assistance of organic co-solvent, co-reagent, phase transfer catalyst or inert atmosphere.[Figure not available: see fulltext.].

Assembly of homoallylamine derivatives through iron-catalyzed three-component sulfonamidoallylation reaction

An efficient FeCl3-catalyzed three-component reaction between aldehydes, sulfonamides and allylsilanes has been achieved, which provides a convenient, atom-economic and green way to construct homoallylamine derivatives. In addition, this reaction exhibits excellent syn stereoselectivity with γ-substituted allylsilanes. A practical three-component cascade process to homoallylamine derivatives is reported, which uses cheap and environmentally benign FeCl3 as catalyst and shows excellent syn stereoselectivity with γ-substituted allylsilanes.

Pd-containing organopolyoxometalates derived from Dawson polyoxometalate [P2W15V3O62]9-: Lewis acidity and dual site catalysis

Grafting of a palladium complex to the Dawson vanadotungstate polyanion [P2W15V3O62]9- via an organic ligand generates a large family of pincer-type hybrid polyoxometalates. The palladium-POM derivatives have dual catalytic properties. Unlike their parent inorganic polyanions, they catalyze allylations while retaining their oxidant character, which leads to single-pot dual site catalysis. This opens a new route for multicatalytic reactions.

Lewis acid-catalyzed oxidative allylation: A new approach for the synthesis of homoallylic alcohols and amines directly from alcohols

A new approach for the synthesis of homoallylic alcohols and amines directly from alcohols via one-pot sequential oxidation-Barbier reaction and oxidation-condensation-Barbier reactions, respectively, is reported. The protocol involves the one-pot ferric chloride-catalyzed oxidation of alcohols to the corresponding aldehydes with chloramine-T followed by indium-mediated Barbier allylation with allyl bromide to afford homoallylic alcohols in 70-90% overall yields. The ferric chloride-catalyzed condensation of aldehydes and oxidation by-product p-toluenesulfonamide followed by indium-mediated Barbier-type allylation of the resulting aldimines with allyl bromide affords homoallylic amines in 60-80% overall yields in the same reaction vessel. The present work demonstrates a new one-pot approach toward homoallylic alcohol and amine synthesis directly from alcohols. Copyright

Indium triflate-catalyzed allylation reactions of N-sulfonyl aldimines or N-alkoxycarbonylamino p-tolylsulfones with allyltrimethylsilane: Synthesis of protected homoallylic amines

Indium triflate-catalyzed allylation reactions of N-sulfonyl aldimines or N-alkoxyloxycarbonylamino p-tolylsulfone with allyltrimethylsilane have been successfully developed to produce protected homoallylic amines.

Transition-metal-free intermolecular amination of sp3 C-H bonds with sulfonamides

An efficient transition-metal-free intermolecular benzylic amidation with sulfonamides is described. Various valuable nitrogen-containing compounds, including amines, β-chloro amine, amino alcohol, α-, β-amino ester, and N-sulfonyl imine, are generated fr

Pd0/SnII promoted Barbier-type allylation and crotylation of sulfonimines

A one-pot Barbier protocol is described for the facile formation of homoallyl sulfonamides from sulfonimines and allyl or crotyl bromide in the presence of SnCl2, and catalytic Pd2(dba)3·CHCl3 at room temperature.

δ and α SP3 C-H bond oxidation of sulfonamides with PhI(OAc)2/I2 under metal-free conditions

(Chemical Equation Presented) An efficient δ and α sp 3 C-H bond oxidation of sulfonamides with PhI(OAc)2/I 2 under metal-free conditions has been reported. The reaction provides a useful route to pyrrolidines, N-sulfonyli

Palladium pincer-complex catalyzed allylation of tosylimines by potassium trifluoro(allyl)borates

(Chemical Equation Presented) Palladium pincer complex 1 catalyzes the reaction of trifluoro(allyl)borate 2 with a wide range of tosylimines (3) under mild and neutral reaction conditions. This catalytic transformation affords homoallylic amines (4) in good to excellent yield. Mechanistic studies suggest that a transmetalation reaction between complex 1 and the borate salt 2 provides an η1-allylpalladium complex, which subsequently reacts with the imine substrate.