Nickel-catalyzed ester carbonylation promoted by imidazole-derived carbenes and salts.

Autor: Yoo C; Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC, USA., Bhattacharya S; Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC, USA., See XY; Eastman Chemical Company, Kingsport, TN, USA., Cunningham DW; Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC, USA., Acosta-Calle S; Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC, USA., Perri ST; Eastman Chemical Company, Kingsport, TN, USA., West NM; Eastman Chemical Company, Kingsport, TN, USA., Mason DC; Eastman Chemical Company, Kingsport, TN, USA., Meade CD; Eastman Chemical Company, Kingsport, TN, USA., Osborne CW; Eastman Chemical Company, Kingsport, TN, USA., Turner PW; Eastman Chemical Company, Kingsport, TN, USA., Kilgore RW; Eastman Chemical Company, Kingsport, TN, USA., King J; Eastman Chemical Company, Kingsport, TN, USA., Cowden JH; Eastman Chemical Company, Kingsport, TN, USA., Grajeda JM; Eastman Chemical Company, Kingsport, TN, USA., Miller AJM; Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC, USA.
Jazyk: angličtina
Zdroj: Science (New York, N.Y.) [Science] 2023 Nov 17; Vol. 382 (6672), pp. 815-820. Date of Electronic Publication: 2023 Nov 16.
DOI: 10.1126/science.ade3179
Abstrakt: Millions of tons of acetyl derivatives such as acetic acid and acetic anhydride are produced each year. These building blocks of chemical industry are elaborated into esters, amides, and eventually polymer materials, pharmaceuticals, and other consumer products. Most acetyls are produced industrially using homogeneous precious metal catalysts, principally rhodium and iridium complexes. We report here that abundant nickel can be paired with imidazole-derived carbenes or the corresponding salts to catalyze methyl ester carbonylation with turnover frequency (TOF) exceeding 150 hour -1 and turnover number (TON) exceeding 1600, benchmarks that invite comparisons to state-of-the-art rhodium-based systems and considerably surpass known triphenylphosphine-based nickel catalysts, which operate with TOF ~7 hour -1 and TON ~100 under the same conditions.
Databáze: MEDLINE
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