4.8 Article

Cyclic (Alkyl)(amino)carbenes (CAACs) in Ruthenium Olefin Metathesis

期刊

ACS CATALYSIS
卷 11, 期 3, 页码 1714-1748

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c05508

关键词

cyclic (alkyl)(amino)carbenes (CAACs); olefin metathesis; homogeneous catalysis; ruthenium catalysts; transition metals

资金

  1. Region Bretagne (ARED 2018 Biometa) [601, 275]
  2. Agence Nationale de la Recherche [ANR-19-276 CE07-0017 ChiCAAC]
  3. U.S. Department of Energy, Office of Science, Basic Energy Sciences, Catalysis Science Program [DE-SC0009376]

向作者/读者索取更多资源

The discovery of cyclic (alkyl)(amino) carbenes (CAACs) in 2005 revolutionized the field of ruthenium olefin metathesis by providing stronger metal-carbene bonds and increased catalytic activity, as demonstrated in patents.
Discovered in 2005, cyclic (alkyl)(amino) carbenes (CAACs) have led to numerous discoveries in the field of ruthenium olefin metathesis, until then largely dominated by the well-known N-heterocyclic carbenes (NHCs). In comparison to the latter, CAACs are simultaneously more nucleophilic (sigma-donating) and electrophilic (pi-accepting), which leads to very strong metal-carbene bonds. Consequently, (CAAC)ruthenium complexes are very robust, which leads to enhanced catalytic activities, as exemplified by the industrially relevant ethenolysis of unsaturated fatty acids (TONs of up to 390000). Herein, we provide a comprehensive overview of the effect of CAAC ligands in olefin metathesis, including results which are described in patents.

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