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- Title
Stable Singlet Carbenes as Organic Superbases.
- Authors
Vermersch, François; Yazdani, Sima; Junor, Glen P.; Grotjahn, Douglas B.; Jazzar, Rodolphe; Bertrand, Guy
- 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(tBu). 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.
- Subjects
CARBENES; BASICITY; ACETONITRILE
- Publication
Angewandte Chemie, 2021, Vol 133, Issue 52, p27459
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202111588