ChemInform Abstract: Functionalization of Some Benzylthioarylboronic Acids by Benzylic Lithiation of Their N‐Butyldiethanolamine Esters or Lithium(triisopropoxy)borates.

Abstract

Esters or Lithium(triisopropoxy)borates. -New arylboronic acids substituted in the benzylic position are synthesized by reaction of protected benzylthioarylboronic acids with various electrophiles. Benzylic lithiation occurs selectively using LDA. The method is also applicable to brominated aryl-benzyl sulfides which are initially transformed into triisopropoxyborates using tert-butyllithium for the first lithiation followed by second lithiation with LDA. Finally, lithiated intermediates are converted to the respective arylboronic acids [cf. (VI)]. -(DURKA, K.; KLIS*, T.; SERWATOWSKI, J.; WOZNIAK, K.; Appl. Organomet. Chem. 25 (2011) 9, 669-674, http://dx.doi.org/10.1002/aoc.1822 ; Fac. Chem., Warsaw Univ. Technol., PL-00-664 Warszawa, Pol.; Eng.) -S. Adam 04-155