89249-38-7

Upstream product

• 6117-91-5 (E/Z)-2-buten-1-ol 
• 873-55-2 sodium benzenesulfonate 
• 106-99-0 buta-1,3-diene 
• 27748-49-8 (Z)-2-nitro-2-butene 
• 160956-36-5 phenyl 3-(trimethylsilyl)but-3-en-1-yl sulfone 
• 13603-84-4 1-(phenylsulfonyl)-2-butyne 
• 13610-03-2 but-2-yn-1-yl(phenyl)sulfide 
• 7205-98-3 chloromethyl phenyl sulfone 
• 884656-75-1 but-3-en-2-yl isobutyl carbonate 
• 24731-39-3 4-(phenylsulfonyl)butan-2-one 
• 702-04-5 crotyl phenyl sulfide 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 38066-16-9 diethyl [(phenylthio)methyl]phosphonate 
• 56069-39-7 diethyl phenylsulfonylmethylphosphonate 

Relevant academic research and scientific papers

Palladium-catalyzed substitution of allylic alcohols with sulfinate salts: A synthesis of bicalutamide

A method is presented for the direct substitution of allylic alcohols with sodium arylsulfinates. The process involves a cooperative action of palladium catalysts, phenylboronic acid and titanium tetraisopropoxide. By taking advantage of this protocol, we achieved a concise synthesis of bicalutamide, an anti-androgen compound for treating prostate cancer.

Isomerisation of Vinyl Sulfones for the Stereoselective Synthesis of Vinyl Azides

Reported is the construction, and facile base-mediated conversation of ten differently substituted 3-azido E-vinyl sulfones (γ-azido-α,β-unsaturated sulfones) into their isomeric vinyl azide counterparts. The requisite 3-azido E-vinyl sulfones were prepared from 3-bromo E-vinyl sulfones, which in turn were accessed from allyl sulfones via a bromination-elimination sequence. In relation to this a one-pot azidation-isomerisation sequence was developed which enabled the direct formation of the vinyl azides from the corresponding 3-bromo E-vinyl sulfones. Similarly, a convenient one-pot Horner–Wadsworth–Emmons olefination-isomerisation approach was utilised in order to prepare some of the allylic sulfones used in this study. The vinyl azide forming process typically proceeded with high levels of Z-selectivity, although this was dependent on the vinyl sulfone substitution pattern. Thus, with either no substituent or a methyl group in the γ- or β-position, relative to the sulfone, good, to high levels of Z-selectivity (Z/E = 85:15 to ≥ 95:5) were obtained. However, incorporation of an α-sulfonyl methyl substituent led to an E-selective process (Z/E = 20:80). A non-bonding interaction between the azido group and the α-sulfonyl vinylic proton is proposed, which acts as a conformational control mechanism to help guide the stereochemical outcome.

Oxidative Allylic Esterification of Alkenes by Cooperative Selenium-Catalysis Using Air as the Sole Oxidant

A new metal-free catalysis protocol for the oxidative coupling of nonactivated alkenes with simple carboxylic acids has been established. This method is predicated on the cooperative interaction of a diselane and a photoredox catalyst, which allows for the use of ambient air or pure O2 as the terminal oxidant. Under the title conditions, a range of both functionalized and nonfunctionalized alkenes can be readily converted into the corresponding allylic ester products with good yields (up to 89%) and excellent regioselectivity as well as good functional group tolerance.

Direct oxidative allylic and vinylic amination of alkenes through selenium catalysis

Bringing "N" into the game: The direct chemoselective nitrogenation of unactivated alkenes can be achieved through oxidative selenium catalysis (see scheme). This method provides a broad variety of allylic imides in yields of up to 89 % using N-fluorobenzenesulfonimide (NFSI) as the terminal oxidant and nitrogen source. Furthermore, an unprecedented selenium-catalyzed vinylic C(sp2)-H nitrogenation was discovered. Copyright

α-Sulfonyl succinimides: Versatile sulfinate donors in Fe-catalyzed, salt-free, neutral allylic substitution

Allyl sulfones are versatile intermediates in organic chemistry. The presence of two distinct functional groups sets the stage for a plethora of subsequent transformations. However, despite these advantages the preparation of regioisomerically enriched sulfones is not easy. The use of sulfinate salts as nucleophiles in substitutions is frequently accompanied by side reactions such as π-bond migration, β-elimination, and so on. Herein we present a preparatively simple way to synthesize a variety of different aryl or alkyl allyl sulfones starting from readily accessible allylic carbonates. By employing aryl or alkyl α-sulfonyl succinimides as sulfinate synthons, mild and regioselective ipso substitution of diverse allylic carbonates was realized.

Reduction of propargylic sulfones to (Z)-allylic sulfones using zinc and ammonium chloride

Propargylic sulfones can be cis-hydrogenated using commercial zinc powder and ammonium chloride in THF-water at room temperature, the major products being the corresponding (Z)-allylic sulfones. Other reducible groups (alkene, benzyloxy) are not affected. Allenylsulfones are implicated in one of the possible reaction pathways.

Tributylstannane: A Highly Efficient Reagent for the Allylation of Radicals

Allylation rates of radicals with tributylstannane (2) have been compared with the ones of the (prop-2-enyl)stannane (3) and stannane (4).The Me3Si substituent showed a rate-accelerating effect (4.2:1

Regioselective Preparation of Allylic Sulfones by Palladium-Catalyzed Reactions of Allylic Nitro Compounds with Sodium Benzenesulfinate

Treatment of allylic nitro compounds with sodium benzenesulfinate in the presence of 5 molpercent of Pd(PPh3)4 in N,N-dimethylformamide (DMF) at 20-70 deg C for 1-10 h resulted in the formation of allylic sulfones with predominance of kinetically controll

Carbon Dioxide-Promoted Telomerization of 1,2- and 1,3-Dienes with Benzenesulfinate Catalyzed by Palladium(0)

The telomerization of 1,2- and 1,3-dienes with benzenesulfinate dihydrate catalyzed by palladium(0) has been promoted by the presence of carbon dioxide