51985-30-9

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 104-55-2 3-phenyl-propenal 
• 104-54-1 3-Phenylpropenol 
• 133039-38-0 tris(4-methylphenyl)bismuthane tosylimide 
• 14371-10-9 (E)-3-phenylpropenal 
• 163926-87-2 4-Methyl-N-[2-((E)-styryl)-1λ⁴-naphtho[1,8-de][1,3]dithiin-(1E)-ylidene]-benzenesulfonamide 
• 24808-73-9 (E)-(3-methoxyprop-1-en-1-yl)benzene 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 59336-59-3 cinnamaldehyde oxime 
• 6873-55-8 p-tolylsulfinyl amide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 120419-99-0 4-phenyl-1-trimethylsilyl-1-azabuta-1,3-diene 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 233770-16-6 (E)-N-(4,4'-diethoxy-1-styrylbut-2-ynyl)-4-toluenesulfonamide 
• 137845-17-1 4-Phenylsulfanylmethyl-2-((E)-styryl)-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole 
• 1031379-06-2 N-((1E,5E)-4,7-dicyano-1-phenylhepta-1,5-dien-3-yl)-4-methylbenzenesulfonamide 
• 1031378-99-0 (E)-N-(4-cyano-1-phenylhexa-1,5-dien-3-yl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures

We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.

Decarboxylative Mannich Reactions with Substituted Malonic Acid Half-Oxyesters

The decarboxylative Mannich reaction between imines and substituted malonic acids half-oxyesters (SMAHOs) has been developed using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst. The reaction proceeds under simple reaction conditions and toler

Strategic vinyl sulfone nucleophile β-substitution significantly impacts selectivity in Vinylogous Darzens and aza-Darzens reactions

Vinylogous Darzens and aza-Darzens reactions employing a benzothiophene 1,1-dioxide nucleophile are reported. These new [2 + 1] annulation reactions, which proceed under mild reaction conditions, are γ-selective, affording trans-epoxides selectively and favoring trans-aziridines. The reactions are base-dependent, with KOtBu and Cs2CO3 being optimal for aldehyde and imine annulations, respectively. Comparison of the benzothiophene nucleophile to its acyclic counterpart reveals superior performance in the case of aldehydes, while the outcome varies depending on the sulfonamide imine used.

A Unified Explanation for Chemoselectivity and Stereospecificity of Ni-Catalyzed Kumada and Cross-Electrophile Coupling Reactions of Benzylic Ethers: A Combined Computational and Experimental Study

Ni-catalyzed C(sp3)-O bond activation provides a useful approach to synthesize enantioenriched products from readily available enantioenriched benzylic alcohol derivatives. The control of stereospecificity is key to the success of these transformations. To elucidate the reversed stereospecificity and chemoselectivity of Ni-catalyzed Kumada and cross-electrophile coupling reactions with benzylic ethers, a combined computational and experimental study is performed to reach a unified mechanistic understanding. Kumada coupling proceeds via a classic cross-coupling mechanism. Initial rate-determining oxidative addition occurs with stereoinversion of the benzylic stereogenic center. Subsequent transmetalation with the Grignard reagent and syn-reductive elimination produce the Kumada coupling product with overall stereoinversion at the benzylic position. The cross-electrophile coupling reaction initiates with the same benzylic C-O bond cleavage and transmetalation to form a common benzylnickel intermediate. However, the presence of the tethered alkyl chloride allows a facile intramolecular SN2 attack by the benzylnickel moiety. This step circumvents the competing Kumada coupling, leading to the excellent chemoselectivity of cross-electrophile coupling. These mechanisms account for the observed stereospecificity of the Kumada and cross-electrophile couplings, providing a rationale for double inversion of the benzylic stereogenic center in cross-electrophile coupling. The improved mechanistic understanding will enable design of stereoselective transformations involving Ni-catalyzed C(sp3)-O bond activation.

Palladium-Catalyzed Direct Intramolecular C-N Bond Formation: Access to Multisubstituted Dihydropyrroles

A palladium-catalyzed intramolecular amination of alkenes with retention of olefin functionalization was achieved under mild reaction conditions. In the presence of palladium catalyst, the tosyl-protected amine can directly couple with a double bond to provide versatile dihydropyrrole derivatives in moderate to excellent yields.

Diastereoselective Synthesis of CF3-Containing Vicinal Diamines

The highly diastereoselective synthesis of CF3-containing vicinal diamines by a convenient two-step procedure without the need to isolate the intermediate products is described.

Lewis Acid Catalyzed Formal [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes and 1-Azadienes: Synthesis of Imine Functionalized Cyclopentanes and Pyrrolidine Derivatives

Lewis acid catalyzed formal [3+2] cycloadditions of 1-azadienes with donor acceptor cyclopropanes to synthesize varieties of imine functionalized cyclopentanes and pyrrolidine derivatives in moderate to high yield have been developed. Moreover, pharmaceut

Nickel-Catalyzed Cross-Electrophile Coupling of Alkyl Fluorides: Stereospecific Synthesis of Vinylcyclopropanes

The stereospecific reductive cross-electrophile coupling reaction of 2-vinyl-4-halotetrahydropyrans for vinylcyclopropane synthesis is reported. The nickel-catalyzed reaction occurs with both alkyl fluorides and alkyl chlorides. To the best of our knowledge, this is the first reported cross-electrophile coupling reaction of an alkyl fluoride. Ring contraction proceeds with high stereospecificity, providing selective synthesis of either diastereomer of di- and trisubstituted cyclopropanes. The utility of this methodology is demonstrated by several synthetic applications including the synthesis of the natural product dictyopterene A. 2-Vinyl-4-fluorotetrahydrofurans also undergo stereospecific ring contractions, providing access to synthetically useful hydroxymethyl cyclopropanes.

Chemoselective Boron-Catalyzed Nucleophilic Activation of Carboxylic Acids for Mannich-Type Reactions

The carboxyl group (COOH) is an omnipresent functional group in organic molecules, and its direct catalytic activation represents an attractive synthetic method. Herein, we describe the first example of a direct catalytic nucleophilic activation of carbox