What question did this study set out to answer?

To establish a mild and metal-free methodology for the synthesis of α-fluoro-α-nitrohomopropargylic amides.

February 19, 2026Asian Journal of Organic Chemistry0 citationsOpen Access

Metal–free Pathway to α ‐Fluoro‐ α ‐nitrohomopropargylic Amides Employing Alkynyliodonium Salts

SShivaniCentral Drug Research Institute AKAzeem KhanLiaquat University of Medical & Health Sciences MZMohd Khalid ZaheerCentral Drug Research Institute

Key Points

To establish a mild and metal-free methodology for the synthesis of α-fluoro-α-nitrohomopropargylic amides.
Developed a direct α-alkynylation process
Utilized alkynyliodonium salts
Employed mild basic conditions
Demonstrated broad substrate scope
Achieved moderate to good yields of amides
Highlighted operational simplicity and ease of handling
Established an environmentally benign synthetic approach

Abstract

ABSTRACT A mild and metal‐free approach has been established for the direct α ‐alkynylation of α ‐fluoro‐ α ‐nitroacetamides, that enabled an efficient synthesis of highly functionalized α ‐fluoro‐ α ‐nitrohomopropargylic amides. The transformation proceeds under mild basic conditions and offers moderate to good yields. This protocol is distinguished by its broad substrate scope, operational simplicity, ease of handling, and environmentally benign approach, making it a valuable tool for the synthesis of a new class of fluorinated building blocks. The strategy was successfully extended for the alkynylation of α ‐cyano‐ α ‐fluoroacetamides.

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