10218-90-3Relevant academic research and scientific papers
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).
Ortho-Specific Bromination of Phenols
Schmitz, Ernst,Pagenkopf, Ingeborg
, p. 998 - 1006 (2007/10/02)
Phenol as well as 3-substituted phenols are brominated exclusively in the ortho positions by N.N-dibromomethylamine, yielding 2.6-dibrominated phenols in excellent yields.Phenols bearing an ortho-substituent need N-bromomethylamine as the brominating agent to take up one bromine atom into the free ortho-position. para-Bromination is not observed in either case. 1-Naphthol gives 2-bromo-1-naphthol, 8-hydroxyquinoline gives 7-bromo-8-hydroxyquinoline with 80percent and 98percent yield respectively. ortho-Specific chlorination of phenols was carried out in some cases using N-chloro-alkylamines.
