154345-34-3Relevant academic research and scientific papers
2-(Chlorodiisopropylsilyl)-6-(trimethylsilyl)phenyl triflate: A modified platform for intramolecular benzyne cycloadditions
Takasu, Kiyosei,Takikawa, Hiroshi,Tawatari, Tsukasa
supporting information, p. 11863 - 11866 (2021/11/30)
2-(Chlorodiisopropylsilyl)-6-(trimethylsilyl)phenyl triflate serves as an efficient aryne precursor for intramolecular benzyne [4 + 2] or (2 + 2 + 2) cycloadditions. Key features of this precursor are (1) rapid connection of various arynophiles to the pre
Continuous-flow synthesis of trimethylsilylphenyl perfluorosulfonate benzyne precursors
Michel, Boris,Greaney, Michael F.
supporting information, p. 2684 - 2687 (2014/06/09)
2-(Trimethylsilyl)phenyl perfluorosulfonated aryne precursors may now be accessed using flow chemistry, enabling the fast preparation of pure compounds with no requirement for low temperature lithiation or column chromatography. The process has been adapted to novel nonaflate precursors, utilizing the cheaper and more user-friendly nonaflyl fluoride reagent. The resultant nonaflates are shown to successfully participate in a range of aryne reaction classes.
Regiocomplementary cycloaddition reactions of boryl- and silylbenzynes with 1,3-dipoles: Selective synthesis of benzo-fused azole derivatives
Ikawa, Takashi,Takagi, Akira,Goto, Masahiko,Aoyama, Yuya,Ishikawa, Yoshinobu,Itoh, Yuji,Fujii, Satoshi,Tokiwa, Hiroaki,Akai, Shuji
, p. 2965 - 2983 (2013/06/26)
Benzo-fused nitrogen-containing heterocycles are abundant in biologically active compounds. One of the most important methods for preparing such heterocycles is the (3 + 2) cycloaddition reaction of benzynes with 1,3-dipolar compounds. However, the reacti
Synthesis of biaryl compounds through three-component assembly: Ambidentate effect of the tert-butyldimethylsilyl group for regioselective diels-alder and hiyama coupling reactions
Akai, Shuji,Ikawa, Takashi,Takayanagi, Sho-Ichi,Morikawa, Yuki,Mohri, Shinya,Tsubakiyama, Masaya,Egi, Masahiro,Wada, Yasufumi,Kita, Yasuyuki
supporting information; experimental part, p. 7673 - 7676 (2009/04/10)
Two for the price of one: A method has been developed for the regiocontrolled synthesis of multisubstituted biaryl derivatives. This protocol involves the use of the tert-butyldimethylsilyl (TBDMS) group to direct the regioselective Diels-Alder reaction of a 3-TBDMS-benzyne with a furan derivative and a subsequent Hiyama cross-coupling reaction of the TBDMS group with aryl iodides (see scheme).
Intramolecular carbolithiation of allyl o-lithioaryl ethers: A new enantioselective synthesis of functionalized 2,3-dihydrobenzofurans
Barluenga, Jose,Fananas, Francisco J.,Sanz, Roberto,Marcos, Cesar
, p. 5397 - 5407 (2007/10/03)
A new and easy method for the diastereoselective synthesis of 3-functionalized 2,3-dihydrobenzofuran derivatives from allyl 2-bromoaryl ethers is described. The key step of this transformation involves an intramolecular carbolithiation reaction of allyl 2-lithioaryl ethers. The substituents in both the allyl and the aryl moieties play an important and decisive role in stopping the reaction at the benzofuran thus avoiding a γ-elimination reaction. Finally, this process is amenable to the synthesis of enantiomerically enriched compounds by using ( - )-sparteine as a chiral inductor.
