- Iridium-Catalyzed Alkylation of Secondary Alcohols with Primary Alcohols: A Route to Access Branched Ketones and Alcohols
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Under borrowing hydrogen conditions, NHC-iridium(I) catalyzed the direct or one-pot sequential synthesis of α,α-disubstituted ketones via the alkylation of secondary alcohols with primary alcohols is reported. Notably, the present approach provides a new method for the facile synthesis of α,α-disubstituted ketones and featured with several characteristics, including a broad substrate scope, using easy-to-handle alcohols as starting materials, and performing the reactions under aerobic conditions. Moreover, the selective one-pot formation of β,β-disubstituted alcohols was achieved by the addition of an external hydrogen source to the reaction mixture.
- Gen?, Serta?,Gülcemal, Süleyman,Günnaz, Salih,?etinkaya, Bekir,Gülcemal, Derya
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p. 9139 - 9152
(2020/08/14)
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- Ruthenium phosphine-pyridone catalyzed cross-coupling of alcohols to form α-alkylated ketones
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An efficient and green route to access diverse functionalized ketones via dehydrogenative-dehydrative cross-coupling of primary and secondary alcohols is demonstrated. Selective and tunable formation of ketones or alcohols is catalyzed by a recently developed proton responsive ruthenium phosphine-pyridone complex. Light alcohols such as ethanol could be used as alkylating agents in this methodology. Moreover, selective tandem double alkylation of isopropanol is achieved by sequential addition of different alcohols.
- Sahoo, Apurba R.,Lalitha, Gummidi,Murugesh,Bruneau, Christian,Sharma, Gangavaram V.M.,Suresh, Surisetti,Achard, Mathieu
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p. 10727 - 10731
(2018/05/31)
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- Ruthenium-NHC Catalyzed α-Alkylation of Methylene Ketones Provides Branched Products through Borrowing Hydrogen Strategy
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The α-alkylation of a broad range of methylene ketones was achieved using a ruthenium(II)-NHC catalyst under borrowing hydrogen conditions. Primary alcohols served as alkylating agents and could be used in a one-to-one stoichiometry with respect to the ketone. The selectivity of the process for methyl over branched ketones enabled a one-pot double alkylation protocol utilizing two different alcohols with a single catalyst. Moreover, this methodology could be applied directly to the one-step synthesis of donepezil, the best-selling drug for the treatment of Alzheimer's disease.
- Schlepphorst, Christoph,Maji, Biplab,Glorius, Frank
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p. 4184 - 4188
(2016/07/12)
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