Reaction of 4-methylphenylboronic acid with CuSCN

July 30, 2024

• Title:       

  Reaction of 4-methylphenylboronic acid (CAS 5720-05-8) with CuSCN

• Image Source:

  A mild copper-catalyzed aerobic oxidative thiocyanation of arylboronic acids with TMSNCS

• Mark:

  Scheme 3

• Associated context:

  For the purpose of investigation of the reaction mechanism, CuSCN was considered as an intermediate and its reactivity on this transformation was examined (Scheme 3). When 0.5 equiv. of CuSCN was reacted with 4-methylphenylboronic acid 1a under the standard procedure, and the corresponding thiocyanate 2a was obtained in 46% yield. In particular, both the ligand TMEDA and O2 were essential for this transformation. Without TMEDA or O2, only trace 2a was observed.