天津
轉自：康龍化成
Access to Terminal Alkynes via Palladium-Catalyzed Coupling of ArCl with a Low Catalyst Loading of 0.08 mol %
Lei Xu, Gen-Qiang Chen,* and Xumu Zhang*
Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry and Medi-X Pingshan, Southern University of Science and Technology, Shenzhen 518055, People’s Republic of China;
Academy for Advanced Interdisciplinary Studies and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518000, People’s Republic of China;
Guangdong Laboratory of Chemistry and Fine Chemical Engineering, Shantou 515031, People’s Republic of China;
—J. Org. Chem. 2025, 90, 23, 7938–7946
Recommended by Chunlei Lu_ MC2
KEY WORDS:Heck?Cassar-Sonogashira reaction, Pd catalysis (反應類型), C(sp2)-C(sp) (成鍵類型), Aryl chlorides. (triisopropylsilyl)-acetylene (原料), Aryl alkynes (產物)
ABSTRACT: The synthesis of terminal alkynes from inexpensive aryl chlorides remains a challenging task in organic synthesis. Here, a Heck?Cassar reaction of aryl chlorides with (triisopropylsilyl)-acetylene catalyzed by low loadings of palladium (0.08 mol %) has been developed. Through subsequent desilylation, aryl-substituted terminal alkynes can be readily prepared. This reaction features robustness and good functional group compatibility, making it suitable for the late-stage modification of drug molecules.
Synthesis of Terminal Alkyne from Aryl Halides
Scope of Aryl Chlorides (Selected)
Scope of Terminal Alkyne
Late-Stage Modification of Drug Molecules
In summary, apractical Heck?Cassar reaction for synthesizing terminal alkynes from aryl chlorides, catalyzed by low loading of palladium (0.08 mol %), has been developed. The transformation is completed in two steps (which can be performed in one pot): the palladium-catalyzed Heck?Cassar reaction of aryl chlorides with (triisopropylsilyl)acetylene, followed by subsequent desilylation. The reaction shows good generality and excellent functional group compatibility and can be used for the late-stage modification of drug molecules on a gram scale.
（轉自：康龍化成）
轉自：市場資訊
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