Primary Alcohols

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Shannon S Stahl - One of the best experts on this subject based on the ideXlab platform.

Huiying Zeng - One of the best experts on this subject based on the ideXlab platform.

  • Dearomatization-Rearomatization Strategy for ortho-Selective Alkylation of Phenols with Primary Alcohols.
    Angewandte Chemie (International ed. in English), 2020
    Co-Authors: Huiying Zeng
    Abstract:

    Phenols are common precursors and core structures of a variety of industrial chemicals, ranging from pharmaceuticals to polymers. However, the synthesis of site-specifically substituted phenols is challenging, and thus the development of new methods for this purpose would be highly desirable. Herein, we report a protocol for palladium-catalyzed ortho -selective alkylation reactions of phenols with Primary Alcohols via a dearomatization-rearomatization strategy, with water as the sole by-product. Various substituted phenols and Primary Alcohols were compatible with the standard reaction conditions. The detailed mechanism of this transformation was also investigated.

  • palladium catalyzed aerobic synthesis of ortho substituted phenols from cyclohexanones and Primary Alcohols
    Chemical Communications, 2020
    Co-Authors: Huiying Zeng
    Abstract:

    Due to the importance of phenols as structural cores and precursors of chemical products, synthesis of site-specific substituted phenols is highly desirable and a significant challenge. An aerobic palladium-catalyzed site-specific synthesis of ortho-substituted phenols from cyclohexanones and Primary Alcohols via an oxidation/aldol/dehydration/aromatization process has been developed. Various substituted cyclohexanones and Primary Alcohols are successfully transformed into ortho-substituted phenols. In addition, this catalytic reaction uses air as the terminal oxidant and generates water as the sole by-product. Furthermore, the method can also be extended to polyhydroxyl substituted substrates with high chemoselectivity between Primary and secondary Alcohols. This method provides a greener tool for synthesizing Primary alkyl ortho-substituted phenols.

Chan Sik Cho - One of the best experts on this subject based on the ideXlab platform.

  • A palladium-catalyzed route for α-alkylation of ketones by Primary Alcohols
    Journal of Molecular Catalysis A: Chemical, 2005
    Co-Authors: Chan Sik Cho
    Abstract:

    Abstract Ketones react with Primary Alcohols in dioxane at 100 °C in the presence of a catalytic amount of Pd/C and KOH along with 1-decene as a sacrificial hydrogen acceptor to give the corresponding coupled ketones in moderate to good yields. The catalytic pathway seems to be proceeded via a sequence involving initial oxidation of Primary Alcohols to aldehydes, cross aldol condensation, and regioselective reduction.

  • Ruthenium-catalyzed regioselective α-alkylation of ketones with Primary Alcohols
    Tetrahedron Letters, 2002
    Co-Authors: Chan Sik Cho, Tae-jeong Kim, Bok Tae Kim, Sang Chul Shim
    Abstract:

    Ketones are regioselectively alkylated with an array of Primary Alcohols in dioxane at 80°C in the presence of a catalytic amount of a ruthenium catalyst together with KOH and a hydrogen acceptor.

  • Ruthenium-catalyzed regioselective -alkylation of ketones with Primary Alcohols
    2002
    Co-Authors: Chan Sik Cho, Tae-jeong Kim, Bok Tae Kim, Sang Chul Shim
    Abstract:

    Ketones are regioselectively alkylated with an array of Primary Alcohols in dioxane at 80°C in the presence of a catalytic amount of a ruthenium catalyst together with KOH and a hydrogen acceptor. © 2002 Elsevier Science Ltd. All rights reserved. -Alkylation of ketones has been known as a fundamental tool for a carbon carbon -bond formation in synthetic organic chemistry. The alkylation is generally achieved by the coupling between nucleophilic enolates (enolate equivalents) and electrophilic alkylating agents and regioselectivity is determined by initial enolate formation. In connection with this report, during the course of our ongoing studies on ruthenium catalysis, we recently found an unusual type of rutheniumcatalyzed transfer hydrogenation of ketones by Primary Alcohols. The reaction gives mainly an unconventional transfer hydrogenated secondary alcohol accompanied by C–C coupling with concomitant formation of an alkylated ketone (Scheme 1). The preferential formaScheme 1. Table 1. Ruthenium-catalyzed -alkylation of 1 with 2 under several conditions Time (h) Hydrogen acceptor Yield (%) Temp. (°C) Entry

Jessica M Hoover - One of the best experts on this subject based on the ideXlab platform.

Aiwen Lei - One of the best experts on this subject based on the ideXlab platform.