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    This document describes the optimization of a Csp-S coupling reaction between TMS-acetylene and substituted thiols using CuO-NPs as a green catalyst. The reaction was carried out at 70°C and produced the desired alkynyl sulfide products in good yields within 6 hours as shown in Table 1. The scope of the reaction is demonstrated by the variety of substituted thiols reacted in Table 2. TLC was used to monitor the reaction as described in Table 3. It was found that preforming the acetylide before adding the thiophenol led to the most efficient reaction conditions. The conclusion states that this CuO-NPs catalyzed reaction provides an inexpensive, efficient, and

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    This document describes the optimization of a Csp-S coupling reaction between TMS-acetylene and substituted thiols using CuO-NPs as a green catalyst. The reaction was carried out at 70°C and produced the desired alkynyl sulfide products in good yields within 6 hours as shown in Table 1. The scope of the reaction is demonstrated by the variety of substituted thiols reacted in Table 2. TLC was used to monitor the reaction as described in Table 3. It was found that preforming the acetylide before adding the thiophenol led to the most efficient reaction conditions. The conclusion states that this CuO-NPs catalyzed reaction provides an inexpensive, efficient, and

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    3 views2 pages

    Cement Supply Chain

    Uploaded by

    44 Charuta Patil
    This document describes the optimization of a Csp-S coupling reaction between TMS-acetylene and substituted thiols using CuO-NPs as a green catalyst. The reaction was carried out at 70°C and produced the desired alkynyl sulfide products in good yields within 6 hours as shown in Table 1. The scope of the reaction is demonstrated by the variety of substituted thiols reacted in Table 2. TLC was used to monitor the reaction as described in Table 3. It was found that preforming the acetylide before adding the thiophenol led to the most efficient reaction conditions. The conclusion states that this CuO-NPs catalyzed reaction provides an inexpensive, efficient, and

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    Csp-S coupling reaction between TMS-acetylene and substituted thiols using CuO-NPs

    Table1: Optimization of reaction conditions for the Csp-S coupling reaction TMS-acetylene and
    substituted thiols using CuO-NPs

    TMS + HS R1 TMS S R1
    TMS-acetylene Substituted Thiophenol Alkynyl Sulfide

    Entry R1 Compound(a) Time(h) Temp(0C) State Appearance Yields M.P/B.P


    (%)(b)
    1 C6H5 1a 6 700C
    2 4-FC6H4 2b 6 700C
    3 4-ClC6H4 3c 6 700C
    4 4-BrC6H4 4d 6 700C

    (a)
    Reaction condition: TMS-acetylene (1.0 mmol), substituted thiophenols (0.500 mmol),
    K2CO3 (0.200 mmol), CuO-NPs (0.200 mmol), DMSO (1.5ml)
    (b)
    Isolated yields
    Table 2: Scope of Csp-S coupling reaction between TMS-acetylene and substituted thiols
    S S S S

    TMS TMS TMS TMS


    F Cl Br
    1a, 2b, 3c, 4d,

    Table 3: TLC monitoring

    Entry R1 Compound(a) Solubility Solvent system Rf value

    1 C6H5 1a EtOAc Hexane: EtOAc (5%), 95:05 v/v


    Hexane Hexane (100%)
    2 4-ClC6H4 2b EtOAc Hexane: EtOAc (5%), 95:05 v/v
    Hexane Hexane (100%)
    3 4-BrC6H4 3c EtOAc Hexane: EtOAc (5%), 95:05 v/v
    Hexane Hexane (100%)
    4 4-FC6H4 4d EtOAc Hexane: EtOAc (5%), 95:05 v/v
    Hexane Hexane (100%)

    Result and Discussion: We want to examine the oxidative cross-dehydrogenative Csp-S


    coupling reaction between tirmethylsilyl acetylene and substituted thiophenols (1a to 4d) as a
    pilot reaction in presence of CuO-NPs as a green catalyst and K2CO3 as base in a DMSO as a
    solvent at 700C. The reaction took place efficiently to produce desired products (1a to 4d).In
    a good yield (Table 1, entry1 to 4)

    Initially we want to form acetylide in the reaction mixtures for that reason we follows
    strategies, first we add TMS-acetylene, K2CO3, CuO-NPs and DMSO .latter thiophenols
    was add after 1.5 hrs in the reaction mixtures. Based on this finding we optimized the
    reaction conditions starting with green catalyst CuO-NPs.

    Conclusion:

    In summary, we analyzed that inexpensive, efficient and eco-friendly CuO-NPs catalyzes the
    oxidative Csp-S cross-dehydrogenative coupling of terminal alkynes and thiophenols to
    developed alkynyl sulfides. This is simple and straightforward as well as atom economic
    strategies is widely applicable to wide range of alkynes and thiols and is compatible with a
    variety of functional groups on the both alkynes and thiols partners. This strategy represents a
    new methodology for highly selective synthesis of alkynyl sulfides

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