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

Morvan, Jennifer; Mauduit, Marc; Bertrand, Guy; Jazzar, Rodolphe

doi:10.1021/acscatal.0c05508

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

Journal Article · Wed Jan 20 00:00:00 EST 2021 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.0c05508· OSTI ID:1773898

^[1]; ^[2]; ^[3]; ^[3]

Univ. de Rennes (France); UCSD
Univ. de Rennes (France)
Univ. of California, San Diego, La Jolla, CA (United States)

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). Compared to the latter, CAACs are simultaneously more nucleophilic (σ-donating) and electrophilic (π-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 (up to of 390,000 TON). Furthermore, we provide a comprehensive overview of the impact of CAAC ligands in olefin metathesis, including results which are discribed in patents.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of California, San Diego, La Jolla, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0009376

OSTI ID:: 1773898

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 3 Vol. 11; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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metathesis
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