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Updated: May 21, 2025
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Automated Alkylation of Heteroaromatic Thioethers with Organozinc Reagents for Library Synthesis
Javier Mazuela1, Aritz Martinez1, Paula Cervantes-Cerrada1
1Global Discovery Chemistry, Chemical Capabilities, Analytical, and Purification, Janssen Research and Development, Janssen-Cilag, S.A., C/Jarama 75, Toledo 45007, Spain.
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In this study, we describe the implementation of an automated high-throughput workflow to efficiently functionalize medicinal-chemistry-relevant heteroaryl thioethers with diverse alkyl organozinc reagents in flow. The successful coupling observed with different aryl thioether substrates and organozinc reagents highlights the broad applicability of this platform for rapid library diversification. This platform greatly improves the speed and efficiency of modifying heteroaromatic thioethers featuring C(sp3) centers, thereby facilitating the discovery of novel bioactive compounds and positioning it as a valuable resource for medicinal chemistry projects.
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Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
02:34Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
02:35Electrophilic Addition to Alkynes: Hydrohalogenation
02:38Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a Ï bond. In alkynes, the presence of two Ï bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...