23703-22-2Relevant articles and documents
Chiral Dibenzopentalene-Based Conjugated Nanohoops through Stereoselective Synthesis
Hermann, Mathias,Wassy, Daniel,Kohn, Julia,Seitz, Philipp,Betschart, Martin U.,Grimme, Stefan,Esser, Birgit
, p. 10680 - 10689 (2021/04/02)
Conjugated nanohoops allow to investigate the effect of radial conjugation and bending on the involved π-systems. They can possess unexpected optoelectronic properties and their radially oriented π-system makes them attractive for host–guest chemistry. Be
Synthesis method of p-bromo-linear alkylbenzene
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Paragraph 0035; 0053, (2017/08/25)
The invention belongs to the technical field of fine chemical industry, and in particular discloses a clean and efficient synthetic process technology of p-bromo-linear alkylbenzene. Paradibromobenzene and linear chain 1-haloalkane are added into an organic solvent, and reaction is conducted under the action of a catalyst ferric acetylacetonate and an activating agent consisting of zinc halide and magnesium powder to obtain the p-bromo-linear alkylbenzene. A paradibromobenzene single coupling technology is adopted, so production of ortho/meta isomers which are difficult to separate is avoided from the source; a Grignard reagent, which is instable to water and air, or an expensive boric acid reagent intermediate is not used, so that the production cost is reduced; a one-pot reaction technology is adopted, so that operation is simplified and good industrial application value is achieved.
Copper-catalyzed alkyl-alkyl cross-coupling reactions using hydrocarbon additives: Efficiency of catalyst and roles of additives
Iwasaki, Takanori,Imanishi, Reiko,Shimizu, Ryohei,Kuniyasu, Hitoshi,Terao, Jun,Kambe, Nobuaki
, p. 8522 - 8532 (2015/01/08)
Cross-coupling of alkyl halides with alkyl Grignard reagents proceeds with extremely high TONs of up to 1230000 using a Cu/unsaturated hydrocarbon catalytic system. Alkyl fluorides, chlorides, bromides, and tosylates are all suitable electrophiles, and a TOF as high as 31200 h-1 was attained using an alkyl iodide. Side reactions of this catalytic system, i.e., reduction, dehydrohalogenation (elimination), and the homocoupling of alkyl halides, occur in the absence of additives. It appears that the reaction involves the β-hydrogen elimination of alkylcopper intermediates, giving rise to olefins and Cu-H species, and that this process triggers both side reactions and the degradation of the Cu catalyst. The formed Cu-H promotes the reduction of alkyl halides to give alkanes and Cu-X or the generation of Cu(0), probably by disproportionation, which can oxidatively add to alkyl halides to yield olefins and, in some cases, homocoupling products. Unsaturated hydrocarbon additives such as 1,3-butadiene and phenylpropyne play important roles in achieving highly efficient cross-coupling by suppressing β-hydrogen elimination, which inhibits both the degradation of the Cu catalyst and undesirable side reactions.
