Copper-Catalyzed Direct Ortho-Alkylation of N-Iminopyridinium Ylides with N-Tosylhydrazones

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• 作者：Qing Xiao ; Lin Ling ; Fei Ye ; Renchang Tan ; Leiming Tian ; Yan Zhang ; Yuxue Li ; Jianbo Wang
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：April 19, 2013
• 年：2013
• 卷：78
• 期：8
• 页码：3879-3885
• 全文大小：450K
• 年卷期：v.78,no.8(April 19, 2013)
• ISSN：1520-6904

文摘

Copper-catalyzed cross-coupling of N-tosylhydrazones with N-iminopyridinium ylides leads to the direct C鈥揌 alkylation. This direct C鈥揌 bond alkylation transformation uses inexpensive CuI as the catalyst without any ligand. The reaction is operationally simple and conducted under mild conditions, giving the corresponding alkylated pyridines in moderate to good yields. DFT calculation provides insights into the reaction mechanism, suggesting that the reaction proceeds through the Cu carbene migratory insertion process.