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H. Doi, I. Ban, A. Nonoyama, K. Sumi, C. Kuang, T. Hosoya, H. Tsukada and M. Suzuki, “Palladium(0)-Mediated Rapid Methylation and Fluoromethylation on Carbon Frameworks by Reacting Methyl and Fluoromethyl Iodide with Aryl and Alkenyl Boronic Acid Esters: Useful for the Synthesis of [11C]CH3–C-and [18F]FCH2-C-Containig PET Tracers (PET = Positron Emission Tomography),” Chemistry—A European Journal, Vol. 15, No. 16, 2009, pp. 4165-4171.

has been cited by the following article:

• TITLE: Evaluation of TlOH Effect for Pd0-Mediated Cross-Coupling of Methyl Iodide and Excess Boronic Acid Ester toward Fabrication of [11C]CH3-Incorporated PET Tracer

  AUTHORS: Hiroko Koyama, Hisashi Doi, Masaaki Suzuki

  KEYWORDS: Synthesis of Short-Lived Positron Emission Tomography Probes; Suzuki-Miyaura-Type Rapid Cross-Coupling; Rapid C-Methylation; TlOH

  JOURNAL NAME: International Journal of Organic Chemistry, Vol.3 No.3, September 25, 2013

  ABSTRACT: The use of thallium(I) hydroxide (TlOH) as a base is known to extremely accelerate the Suzuki-Miyaura cross-coupling reaction using organoboronic acid or organoboronic acid ester as a substrate. Here, we investigated the effects of TlOH by comparing with other conventional bases such as KOH, K2CO3, and CsF for Pd0-mediated rapid cross-coupling reactions between CH3I and organoborane reagents, such as phenyl-, (Z)-4-benzyloxy-2-butenyl-, and benzylboronic acid pinacol esters under the conditions CH3I/borane/Pd0/base (1:40:1:3) in THF/H2O or DMF/H2O for 5 min with an aim to fabricate a PET tracer efficiently. Consequently, however, the use of TlOH was much less efficient than the other bases for the acceleration of cross-coupling reactions. Thus, it was reconfirmed that the milder and non-toxic conditions using K2CO3 or CsF so far developed by our group were most appropriate for the rapid C-methylations.