Cleavage of Carbodicarbenes with N 2 O for Accessing Stable Diazoalkenes: Two‐Fold Ligand Exchange at a C(0)‐Atom
Year: 2024
Type: article
Abstract: The cleavage of carbophosphinocarbenes and carbodicarbenes with nitrous oxide (N 2 O) leads to the formation of room‐temperature stable diazoalkenes. The utility of Ph 3 P/N 2 and NHC/N 2 ligand exchange reactions were demonstrated by accessing novel benzimidazole‐ and benzothiazole derived diazoalkenes, which are not accessible by the current state‐of‐the‐art methods. The stable diazoalkenes subsequently allow further ligand exchange reactions at C(0) with carbon monoxide, isocyanide, or a diamidocarbene (DAC). Overall, the combination of hitherto unknown NHC/N 2 and N 2 /L (L = DAC, CO, R−NC) ligand exchange reactions at a C(0) center allow the selective functionalization of the carbodicarbene ligand structure which represents a new methodology to rapidly assemble novel carbodicarbenes or cumulenic compounds.
Authors: Yijie He, Yichong Lyu, David Tymann, Patrick W. Antoni, Max M. Hansmann
Institution: TU Dortmund University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $5,510
OpenAlex ID: W4402319407