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Synthesis 2021; 53(21): 4097-4109
DOI: 10.1055/s-0037-1610781
DOI: 10.1055/s-0037-1610781
paper
Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- and Alkynylnaphthoquinones and Derivatives
The authors acknowledge the financial support from Brazil’s governmental agencies (CAPES, FAPERJ, and CNPq).
Abstract
Functionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free CuI-mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.
Key words
Castro–Stephens coupling - cycloaddition - Heck reaction - lithium chloride - Sonogashira reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610781.
- Supporting Information
Publication History
Received: 22 January 2021
Accepted after revision: 06 July 2021
Article published online:
23 August 2021
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