Direct Access to Aryl Bis(trifluoromethyl)carbinols from Aryl Bromides or Fluorosulfates: Palladium-Catalyzed Carbonylation
Katrine Domino
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
These authors contributed equally to this work.
Search for more papers by this authorCedrick Veryser
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, Belgium
These authors contributed equally to this work.
Search for more papers by this authorBenjamin A. Wahlqvist
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
Search for more papers by this authorCecilie Gaardbo
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
Search for more papers by this authorDr. Karoline T. Neumann
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
Search for more papers by this authorProf.Dr. Kim Daasbjerg
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
Search for more papers by this authorProf. Dr. Wim M. De Borggraeve
Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, Belgium
Search for more papers by this authorCorresponding Author
Prof. Dr. Troels Skrydstrup
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
Search for more papers by this authorKatrine Domino
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
These authors contributed equally to this work.
Search for more papers by this authorCedrick Veryser
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, Belgium
These authors contributed equally to this work.
Search for more papers by this authorBenjamin A. Wahlqvist
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
Search for more papers by this authorCecilie Gaardbo
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
Search for more papers by this authorDr. Karoline T. Neumann
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
Search for more papers by this authorProf.Dr. Kim Daasbjerg
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
Search for more papers by this authorProf. Dr. Wim M. De Borggraeve
Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, Belgium
Search for more papers by this authorCorresponding Author
Prof. Dr. Troels Skrydstrup
Carbon Dioxide Activation Center (CADIAC), Department of Chemistry and the Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark
Search for more papers by this authorGraphical Abstract
The more the merrier: Described is the direct synthesis of aryl bis(trifluoromethyl)carbinols from aryl bromides and fluorosulfates with a stoichiometric amount of carbon monoxide and two equivalents of trifluoromethyltrimethylsilane. The method exhibits good yields, broad scope, and good functional-group tolerance, and is suitable for carbon-isotope labeling.
Abstract
A palladium-catalyzed carbonylative approach for the direct conversion of (hetero)aryl bromides into their α,α-bis(trifluoromethyl)carbinols is described, and it employs only stoichiometric amounts of carbon monoxide and trifluoromethyltrimethylsilane. In addition, aryl fluorosulfates proved highly compatible with these reaction conditions. The method is tolerant of a diverse set of functional groups, and it is adaptable to late-stage carbon-isotope labeling.
Supporting Information
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