78388-17-7

Upstream product

• 504-61-0 (E)-but-2-enol 
• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 
• 598-32-3 2-hydroxy-3-butene 
• 70-55-3 toluene-4-sulfonamide 
• 95602-06-5 O-but-3-en-2-yl N-tosylcarbamate 
• 56930-04-2 trans-crotylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 4083-64-1 Tosyl isocyanate 
• 941-55-9 4-toluenesulfonyl azide 
• 1309474-14-3 C₁₆H₂₂BrNO₄S 
• 286376-23-6 4-methyl-N-(prop-1-yn-1-yl)benzenesulfonamide 
• 1186219-42-0 N-allyl-4-methyl-N-(3-methylbuta-1,2-dienyl)benzenesulfonamide 
• 106-51-4 p-benzoquinone 
• 4784-77-4 (E/Z)-crotyl bromide 

Downstream Products

• 50401-85-9 (E)-N-(but-2-en-1-yl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 
• 1063751-13-2 (E)-N-(but-2-enyl)-N-(2-cyclopropylideneethyl)-4-methylbenzenesulfonamide 
• 1256265-29-8 C₂₀H₂₉NO₂SSi 
• 1256265-28-7 C₁₉H₂₇NO₂SSi 
• 928154-53-4 (E)-N-(but-2-enyl)-4-methyl-N-(phenylethynyl)benzenesulfonamide 

Relevant academic research and scientific papers

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.

Copper-Catalyzed Azide–Ynamide Cyclization to Generate α-Imino Copper Carbenes: Divergent and Enantioselective Access to Polycyclic N-Heterocycles

Here an efficient copper-catalyzed cascade cyclization of azide-ynamides via α-imino copper carbene intermediates is reported, representing the first generation of α-imino copper carbenes from alkynes. This protocol enables the practical and divergent synthesis of an array of polycyclic N-heterocycles in generally good to excellent yields with broad substrate scope and excellent diastereoselectivities. Moreover, an asymmetric azide–ynamide cyclization has been achieved with high enantioselectivities (up to 98:2 e.r.) by employing BOX-Cu complexes as chiral catalysts. Thus, this protocol constitutes the first example of an asymmetric azide–alkyne cyclization. The proposed mechanistic rationale for this cascade cyclization is further supported by theoretical calculations.

Regioselective Wacker-Type Oxidation of Internal Olefins in tBuOH Using Oxygen as the Sole Oxidant and tBuONO as the Organic Redox Cocatalyst

A regioselective Wacker-Tsuji oxidation of internal olefins in tBuOH has been developed using oxygen as the terminal oxidant and tert-butyl nitrite as the simple organic redox cocatalyst without the involvement of hazardous cocatalysts or harsh reaction conditions. A series of internal olefins bearing various functional groups can be oxidized to the corresponding substituted ketones in generally good yields with high regioselectivities.

Cobalt-Catalyzed Tandem Radical Cyclization/C-C Coupling Initiated by Directed C-H Activation

A cobalt-N-heterocyclic carbene catalyst promotes a tandem radical cyclization/C-C coupling reaction between tosylamide-tethered bromo-alkenes and aryl N-H imines initiated by chelation-assisted arene C-H activation, affording 3-(arylmethyl)pyrrolidine de

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

Highly efficient mesoporous polymer supported phosphine-gold(i) complex catalysts for amination of allylic alcohols and intramolecular cyclization reactions

A series of novel heterogeneous gold(i) catalysts were synthesized by immobilizing gold(i) complexes on ordered mesoporous polymer FDU-15 and characterized by XRD, N2 adsorption-desorption, FT-IR, TEM, EDS, etc. The catalytic activities of thes

Palladium-Catalyzed Intermolecular Oxidative Cyclization of Allyltosylamides with AcOH: Assembly of 3-Pyrrolin-2-ones

The first example of Pd-catalyzed oxidative cyclization of allyltosylamides with acetic acid is reported. This transformation involved C-N/C-C bond formation and provided 3-pyrrolin-2-ones in a one-pot manner with easy-operation, excellent atom economy and good yields. Mechanistic studies indicate that the reaction proceeds through intermolecular aminopalladation, migratory insertion, reinsertion and β-hydride elimination processes.

Ligand-Controlled Cobalt-Catalyzed Transfer Hydrogenation of Alkynes: Stereodivergent Synthesis of Z- and E-Alkenes

Herein, we report a novel cobalt-catalyzed stereodivergent transfer hydrogenation of alkynes to Z- and E-alkenes. Effective selectivity control is achieved based on a rational catalyst design. Moreover, this mild system allows for the transfer hydrogenation of alkynes bearing a wide range of functional groups in good yields using catalyst loadings as low as 0.2 mol %. The general applicability of this procedure is highlighted by the synthesis of more than 50 alkenes with good chemo- and stereoselectivity. A preliminary mechanistic study revealed that E-alkene product was generated via sequential alkyne hydrogenation to give Z-alkene intermediate, followed by a Z to E alkene isomerization process.

A New Approach to Non-Coordinating Anions: Lewis Acid Enhancement of Porphyrin Metal Centers in a Zwitterionic Metal-Organic Framework

We describe a new strategy to generate non-coordinating anions using zwitterionic metal-organic frameworks (MOFs). By assembly of anionic inorganic secondary building blocks (SBUs) ([In(CO2)4]-) with cationic metalloporphyrin-based organic linkers, we prepared zwitterionic MOFs in which the complete internal charge separation effectively prevents the potential binding of the counteranion to the cationic metal center. We demonstrate the enhanced Lewis acidity of MnIII- and FeIII-porphyrins in the zwitterionic MOFs in three representative electrocyclization reactions: [2 + 1] cycloisomerization of enynes, [3 + 2] cycloaddition of aziridines and alkenes, and [4 + 2] hetero-Diels-Alder cycloaddition of aldehydes with dienes. This work paves a new way to design functional MOFs for tunable chemical catalysis.

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.