The superbase-mediated pairwise substitution of the 2,2'- and 6,6'-positions in a biphenyl derivative
The superbasic mixt. of butyllithium and potassium tert-butoxide is powerful enough to enable the double proton abstraction from one ortho and one ortho' position of 4,4'-di-tert-butylbiphenyl. In this way, a series of functionalized derivs. becomes readily accessible, among them 4,4'-di-tert-butylbiphenyldiyl-2,2'-dicarboxylic acid and 4,4'-di-tert-butylbiphenyl-2,2'-diol. The latter compd. can be subjected again to a superbase-promoted double metalation, thus giving rise to 2,2',6,6'-tetrasubstituted biphenyl derivs. [on SciFinder (R)]
WOS:000220048400009
2004
5
1014
1017
CAN 140:374942 25-10 Benzene, Its Derivatives, and Condensed Benzenoid Compounds Institut de Chimie moleculaire et biologique,Ecole Polytechnique Federale,Lausanne,Switz. Journal 1434-193X written in English. 58775-13-6P Role: BYP (Byproduct), PREP (Preparation) (prepn. of 2,2'- and 6,6'-substituted biphenyls via superbasic mixt. of butyllithium and potassium tert-butoxide for double proton abstraction and subsequent metalation); 1625-91-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of 2,2'- and 6,6'-substituted biphenyls via superbasic mixt. of butyllithium and potassium tert-butoxide for double proton abstraction and subsequent metalation); 63992-30-3P; 685108-66-1P; 685108-69-4P; 685108-71-8P; 685108-72-9P; 685108-73-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of 2,2'- and 6,6'-substituted biphenyls via superbasic mixt. of butyllithium and potassium tert-butoxide for double proton abstraction and subsequent metalation); 109-72-8 (Butyllithium); 865-47-4 Role: RGT (Reagent), RACT (Reactant or reagent) (prepn. of 2,2'- and 6,6'-substituted biphenyls via superbasic mixt. of butyllithium and potassium tert-butoxide for double proton abstraction and subsequent metalation); 32750-01-9P; 70728-89-1P; 70728-91-5P; 70728-93-7P; 70728-95-9P; 84405-38-9P; 107208-71-9P; 685108-67-2P; 685108-68-3P; 685108-70-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of 2,2'- and 6,6'-substituted biphenyls via superbasic mixt. of butyllithium and potassium tert-butoxide for double proton abstraction and subsequent metalation)
REVIEWED
EPFL