4.6 Article

New Vistas in Transmetalation with Discrete AgCF3 Species: Implications in Pd-Mediated Trifluoromethylation Reactions

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 46, Pages 11895-11898

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201802586

Keywords

organometallic synthesis; silver; structural elucidation; transmetalation; trifluoromethylation

Funding

  1. CERCA Programme/Generalitat de Catalunya
  2. Spanish Ministry of Economy, Industry and Competitiveness [MINECO: CTQ2017-87792-R, CTQ2016-79942-P, CTQ2015-64436-P]
  3. La Caixa-Severo Ochoa programme
  4. Spanish Ministry of Economy, Industry and Competitiveness (AIE/FEDER, EU)
  5. Spanish Ministry of Economy, Industry and Competitiveness (Severo Ochoa Excellence Accreditation 2014-2018) [SEV-2013-0319]

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This work describes the employment of discrete AgCF3 complexes as efficient transmetalating agents to Pd-II to surmount overlooked challenges related to the transmetalation step in Pd-catalyzed trifluoromethylation processes. We report the participation of a unique silver ate (Cs)[Ag(CF3)(2)] complex, under stoichiometric and catalytic conditions, in the unprecedented one-pot formation of PhCF3 using PhI as starting material. Moreover, we show that the transmetalation step, which is often ignored in these transformations, can also determine the success or failure of the coupling process.

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