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Stable Singlet Carbenes as Organic Superbases.
Vermersch, François; Yazdani, Sima; Junor, Glen P; Grotjahn, Douglas B; Jazzar, Rodolphe; Bertrand, Guy.
Afiliação
  • Vermersch F; UCSD-CNRS Joint Research Laboratory (IRL 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA, 92093-0358, USA.
  • Yazdani S; UCSD-CNRS Joint Research Laboratory (IRL 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA, 92093-0358, USA.
  • Junor GP; Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Drive, San Diego, CA, 92182-1030, USA.
  • Grotjahn DB; UCSD-CNRS Joint Research Laboratory (IRL 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA, 92093-0358, USA.
  • Jazzar R; Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Drive, San Diego, CA, 92182-1030, USA.
  • Bertrand G; UCSD-CNRS Joint Research Laboratory (IRL 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA, 92093-0358, USA.
Angew Chem Int Ed Engl ; 60(52): 27253-27257, 2021 Dec 20.
Article em En | MEDLINE | ID: mdl-34729888
ABSTRACT
A simple experimental procedure for scaling carbene Brønsted basicity is described. The results highlight the strong basicity of pyrazol-4-ylidenes, a type of mesoionic carbene, also named cyclic-bentallenes (CBA). They are more basic (pKaH >42.7 in acetonitrile) than the popular proazaphosphatrane Verkade bases, and even the Schwesinger phosphazene superbase P4 (t Bu). The basicity of these compounds can readily be tuned, and they are accessible in multigram quantities. These results open new avenues for carbon centered superbases.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2021 Tipo de documento: Article
Texto completo
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PubMed Links
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2021 Tipo de documento: Article