38610-96-7

Upstream product

• 119-61-9 benzophenone 
• 100-41-4 ethylbenzene 
• 2042-85-5 1,2-diphenylpropan-1-one 
• 591-51-5 phenyllithium 
• 672-65-1 (1-chloroethyl)benzene 
• 872610-99-6 1-dimethylstibanyl-1-phenylethane 
• 585-71-7 (1-bromoethyl)benzne 

Downstream Products

• 3677-70-1 1,1,2-triphenylprop-1-ene 
• 854256-42-1 (+/-)-methyl-(1.1.2-triphenyl-propyl)-ether 
• 112949-16-3 2,2,3-triphenyl-butyric acid 

Relevant academic research and scientific papers

Generation of carbanions through stibine-metal and bismuthine-metal exchange reactions and its applications to precision synthesis of ω-end-functionalized polymers

Generation of carbanions from organostibines and organobismuthines through heteroatom-metal exchange reactions was examined from synthetic and mechanistic viewpoints. The exchange reaction proceeded spontaneously upon treatment with various organometallic reagents, such as alkyl lithiums, tetraalkyl zincates, and alkyl magnesium halides to afford the corresponding carbanions quantitatively. Due to the high reactivity of these heteroatom compounds, the exchange reactions took place exclusively even in the presence of various polar functional groups, which potentially react with organometallic species. The advantage of this method was exemplified by the end-group transformation of living polymers that bear these heteroatom species at the ω-polymer end, prepared by using organostibine and bismuthine-mediated living radical polymerizations. Various polymers that bear polar functional groups and acidic hydrogen-for example, poly(methyl methacrylate), poly(butyl acrylate), poly(N-isopropyl acrylamide), and poly(2-hydroxyethyl methacrylate)-could be used in the exchange reactions, and subsequent trapping with electrophiles afforded the corresponding polymers with controlled molecular weights, molecular weight distributions, and end-group functionalities. Competition experiments showed that organostibines and organobismuthines were among the most reactive heteroatom compounds towards organometallic reagents and that their high reactivity was responsible for the high chemoselectivity in the exchange reaction. All's well that ends well: The generation of carbanions from organostibine and -bismuthine compounds was achieved thorough a heteroatom-metal exchange reaction (see scheme). The highly chemoselective exchange reaction could be applied to precision synthesis of varieties of ω-end- functionalized polymers that possess a polar functional group.

Reactivity of the secondary benzylic Grignard reagent from 1-phenylethyl chloride with aldehydes and ketones. More evidence for the rearrangement mechanism in benzyl Grignard reactions

Additional evidence for the mechanism proposed previously to account for diol formation in the reaction of the Grignard reagent from benzyl chloride with aldehydes has been obtained from a study of the interaction of the Grignard reagent from 1-phenylethyl chloride with carbonyl compounds.This Grignard reagent reacts with ketones (except non-enolisable ketones) to give normal alcohols in low yields, and with aldehydes to give diols.However, in contrast to that formed in the reaction of benzylmagnesium chloride, an unstable trienic alcohol formed from the rearrangement of the corresponding alkoxide could be isolated in some case as the major product, providing confirmatory evidence for the existence of an initial reversible rearrangement in the reaction of the benzylic Grignard reagents with carbonyl compounds.

Easy access to secondary and tertiary alcoholsviametal-free and light mediated radical carbonyl allylation

Here we report a strategy for carbonyl addition with unactivated alkenes using an organic photocatalyst on both aldehyde and ketone substrates. This protocol grants us a good alternative to the traditional Barbier-Grignard allylation that exhibits poor functional group tolerance. With this method the stoichiometric use of metals can be avoided, high atom economy can be achieved and fewer by-products are generated.

Visible-Light Photoredox Enables Ketone Carbonyl Alkylation for Easy Access to Tertiary Alcohols

Being a handle for synthesizing quaternary carbon centers and olefins, together with ubiquitous appearance in organic building blocks, makes tertiary alcohols valuable targets in synthesis. However, traditional syntheses of these alcohols have faced several challenges including the employment of functionalized reactive reagents, undesirable side reactions, and decomposition of the alcohol products under harsh conditions. The paucity of a synthetic approach to bulky tertiary alcohols prompts our interest to develop a benign catalytic protocol to tackle the current issues. Here, we have successfully demonstrated the use of ketyl radicals in intermolecular cross radical-radical coupling, which has opened a different door for accessing complex tertiary alcohols. On the other hand, by starting from feedstock and naturally derived chemicals without any pre-activation, it would be superior to traditional methodologies in the industrial context.

Chemoselective Preparation of Ketones by the Grignard Reaction of N-Acylpyrazoles

N-Acylpyrazoles afford chemoselectively the corresponding ketones in good yields by the use of equimolar amounts of Grignard reagent.In the case of an optically active N-acylpyrazole, optical asymmetry was retained in comparable optical yield.Ketone formation by the Grignard reactions can be regarded as an important functionalization in a synthetic loop using pyrazoles as the auxiliary compound.

Generation of allyl- and benzyllithiums from the corresponding halides by the aid of lithium-tellurium exchange reactions

A variety of allyl- and benzyllithiums were prepared by lithium-tellurium exchange reactions of allylic and benzylic tellurides generated in situ from the corresponding halides.The produced organolithiums were trapped successfully with electrophiles such as aldehydes, ketones, and trimethylchlorosilane.Benzyllithiums having an alkyl, alkoxy,fluoro, chloro, or cyano substituent(s) on their aromatic ring were generated efficiently in THF.Benzylic tellurides bearing a bromo or iodo substituent afforded a mixture of products under similar conditions arising from the competing lithium-halogen exchange and/or the displacement of the halogen atom with organolithiums used, but they were converted selectively to benzyllithiums in ether without affecting halogen substituents on the benzene ring.Several allyllithiums including dilithioisobutene were generated from allylic halides in a similar way via allylic tellurides.Wurtz-type coupling was negligible in any reactions examined. Key words: Tellurium; Lithium; Allyl; Benzyl; Halide