17164-88-4

Upstream product

• 873-55-2 sodium benzenesulfonate 
• 2506-41-4 1-chloromethylnaphthalene 
• 325-46-2 N,N,N-trimethyl-1-(naphthalene-2-yl)methanaminium iodide 
• 80-17-1 benzenesufonyl hydrazide 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 1592-38-7 2-Naphthalenemethanol 
• 108-98-5 thiophenol 
• 122408-45-1 (naphthalen-2-ylmethyl)(phenyl)sulfane 

Downstream Products

• 30246-73-2 (E)-2-(β-naphthyl)-1-(phenylsulfonyl)ethene 
• 1208999-05-6 C₂₉H₂₄O₃S₂ 
• 1160295-34-0 2-(1-(phenylsulfonyl)ethyl)naphthalene 

Relevant academic research and scientific papers

A general and practical sulfonylation of benzylic ammonium salts with sulfonyl hydrazides for the synthesis of sulfones

A practical and efficient approach adopting transition-metal-free cross-coupling of sulfonyl hydrazides with benzyl ammonium salts has been developed to synthesize benzyl sulfones using Cs2CO3 as base under mild conditions. The protocol employs stable and easy to handle coupling partners, and is endowed with good substrate compatibility, leading to functional benzyl sulfones in good yields.

Base-controlled divergent synthesis of vinyl sulfones from (benzylsulfonyl)benzenes and paraformaldehyde

A tuneable metal-free protocol for the selective preparation of a-substituted vinyl sulfone and (E)-vinyl sulfone derivatives has been described. In this process, stable paraformaldehyde was used as the carbon source. The base played an important role in the selectivity control of transformations. More than 50 products were synthesized with excellent chemoselectivity and broad functional group tolerance.

Manganese-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols with Sulfones: A Tool to Access Highly Substituted Vinyl Sulfones

The development of first-row-transition-metal catalysts that can match with the reactivities of the noble metals is considered to be challenging yet very much a desirable goal in homogeneous catalysis. It has become even more fascinating to develop processes where these metals show a unique reactivity and selectivity than their higher congeners. Herein, we report on the catalytic activity of a pincer complex of the abundant earth metal manganese for an unprecedented acceptorless dehydrogenative coupling of alkyl sulfones with alcohols. Thus, highly functionalized vinyl sulfones were obtained in moderate to good yields. Both benzylic and aliphatic alcohols could be utilized, and several functional groups including bromides and iodides are tolerated under the reaction conditions. The reaction is environmentally benign, producing dihydrogen and water as byproducts. Preliminary mechanistic experiments involving kinetic, deuterium-labeling, and NMR experiments were performed.

Remote Nucleophilic Allylation by Allylrhodium Chain Walking

Metal migration through a carbon chain is a versatile method for achieving remote functionalization. However, almost all known examples involve the overall net migration of alkylmetal species. Here, we report that allylrhodium species obtained from hydrorhodation of 1,3-dienes undergo chain walking toward esters, amides, or (hetero)arenes over distances of up to eight methylene units. The final, more highly conjugated allylrhodium species undergo nucleophilic allylation with aldehydes and with an imine to give Z-homoallylic alcohols and amines, respectively.

Preparation of Quaternary Centers via Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Tertiary Sulfones

We describe the development of a nickel-catalyzed Suzuki-Miyaura cross-coupling of tertiary benzylic and allylic sulfones with arylboroxines. A variety of tertiary sulfones, which can easily be prepared via a deprotonation-alkylation route, were reacted to afford symmetric and unsymmetric quaternary products in good yields. We highlight the use of either BrettPhos or Doyle's phosphines as effective ligands for these challenging desulfonative coupling reactions. The utility of this methodology was demonstrated in the concise synthesis of a vitamin D receptor modulator analogue.

PROCESS FOR THE MANUFACTURE OF BENZYLSULFONYLARENES

The present invention provides a process for the manufacture of an arylmethyl-sulfonylarene, R1CH2SO2R2, wherein R1 and R2 are each independently an optionally substituted phenyl or naphthyl group which process comprises reacting an arylmethylhalide, R1CH2-Hal wherein R1 is as defined hereinabove and Hal is Cl, Br or I with a sodium arylsulfinate R2SO2Na wherein R2 is as defined hereinabove in the presence of a base optionally in the presence of a solvent. Also provided is the use of the inventive process in the manufacture of a 3-arylsulfonylindazole 5-HT6 ligand.

Double elimination protocol for the synthesis of arylene ethynylenes containing heteroaromatic rings

The double elimination reaction of β-substituted sulfones offers a versatile strategy for synthesis of arylene ethynylene kits containing heteroaromatic rings. A sequence of aldol reaction between α-sulfonyl carbanion and aldehyde, trapping the resulting aldolate to give β-substituted sulfone, and double elimination of this intermediate can be integrated in one pot. This protocol allows thiophene, pyridine, and ferrocene units to be accommodated in phenylene ethynylene arrays.

Tandem Enyne Allene-Radical Cyclization: Low-Temperature Approaches to Benz[e]indene and Indene Compounds

In an effort to lower the temperatures required to prepare multicyclic compounds using the tandem enediyne-radical cyclization, we have developed the tandem enyne allene-radical cyclization which proceeds at temperatures as low as 37°C. The reactions were

Tandem enyne allene-radical cyclization via base-catalyzed isomerization of enediyne sulfones

Enediyne sulfones 12-16 undergo a base-catalyzed isomerization to the corresponding enyne allenes followed by a tandem enyne allene-radical cyclization at 37°C to provide 2,3-dihydrobenz[e]indenes 17-21 in good yields.