72863-24-2Relevant academic research and scientific papers
Palladium-catalyzed substitution of allylic alcohols with sulfinate salts: A synthesis of bicalutamide
Jhang, Yin-Jia,Chang, Chieh-Yu,Lin, Yu-Huan,Lee, Chein-Chung,Wu, Yen-Ku
supporting information, (2021/05/04)
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
Collins, Niall,Connon, Robert,Evans, Paul,Sánchez-Sanz, Goar
supporting information, p. 6228 - 6235 (2020/10/02)
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
Ortgies, Stefan,Depken, Christian,Breder, Alexander
supporting information, p. 2856 - 2859 (2016/07/06)
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
Trenner, Johanna,Depken, Christian,Weber, Thomas,Breder, Alexander
supporting information, p. 8952 - 8956 (2013/09/02)
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
Jegelka, Markus,Plietker, Bernd
, p. 10417 - 10430 (2011/10/31)
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.
Aluminum chloride-iron promoted coupling of sulfonyl chlorides with alkyl halides in aqueous media
Saikia, Promod,Laskar, Dhrubojyoti D.,Prajapati, Dipak,Sandhu, Jagir S.
, p. 512 - 513 (2007/10/03)
A simple and inexpensive procedure for the coupling of sulfonyl chlorides and alkyl halides with aluminum chloride-iron system at ambient temperature in high yield is achieved in aqueous media.
Bi or Cd-induced coupling of sulfonyl chlorides with allylic halides. A simple synthesis of allylic sulfones
Baruah, Mukulesh,Boruah, Anima,Prajapati, Dipak,Sandhu, Jagir S.
, p. 1083 - 1084 (2007/10/03)
The bismuth or cadmium-catalyzed coupling reaction between aryl and alkyl sulfonyl chlorides and allylic halides proceeds smoothly to provide excellent yields of allylic sulfones at ambient temperature.
Diastereoselectivity of the conjugate addition of organocopper reagents to (E)-γ-hydroxy-α,β-unsaturated sulfones
Dominguez,Carretero
, p. 5803 - 5806 (2007/10/02)
The conjugate addition of organocopper reagents, mainly the higher order cuprates R3CuLi2 to (E)-γ-hydroxy-α,β-unsaturated phenyl sulfones takes place with excellent yields and high anti-selectivity.
Stereoselective preparation of vinyl sulfones by protodesilylation of allyl silanes
Funk, Raymond L.,Umstead-Daggett, Joy,Brummond, Kay M.
, p. 2867 - 2870 (2007/10/02)
Allyl sulfones can be conjugated to furnish vinyl sulfones via allyl silane intermediates. The stereoselectivity observed in the protodesilylation step provides a new method for stereoselective preparation of (E)-di-and tri substituted vinyl sulfones.
