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Updated: May 10, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Minisci Reaction by an MW-Boost: A Simple Protocol for Site-Selective Dehydrogenative Cross-Coupling Between
Syuan-Ping Jou1, Yen-Ku Wu1, Takahide Fukuyama2
1Department of Applied Chemistry, National Yang Ming Chiao Tung University, Hsinchu, Taiwan.
None:
The Minisci-type reaction between C(sp3)─H bonds and nitrogen-containing aromatics was carried out using a simple protocol based on the persulfate anion (PS) under microwave (MW) irradiation. The MW/PS protocol is applicable to a wide variety of dehydrogenative coupling reactions of N-heteroaromatics and C(sp3)─H bonds, leading to the formation of alkylated heteroaromatics. Site-selectivity is ensured by hydrogen atom transfer (HAT) with the sulfate radical affecting the polar/steric effects in the transition state. The MW/PS protocol was applicable to direct intramolecular cyclization to give five and six-membered rings fused by pyridine and lutidine, which, in previous methods, it was necessary to use tedious derivatization to imino-oxyacetic acids as HAT precursors.
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