Copper-Catalyzed Transformation of Hydrazones into Halogenated Azabutadienes, Versatile Building Blocks for Organic Synthesis

详细信息    查看全文

• 作者：Valentine G. NenajdenkoAlexey V. Shastin ; Vladimir M. Gorbachev ; Sergey V. Shorunov ; Vasiliy M. Muzalevskiy ; Anna I. Lukianova ; Pavel V. Dorovatovskii ; Victor N. Khrustalev
• 刊名：ACS Catalysis
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：7
• 期：1
• 页码：205-209
• 全文大小：476K
• ISSN：2155-5435

文摘

A one-step copper-catalyzed reaction of aldehyde-derived N-substituted hydrazones with CCl₄ resulted in efficient synthesis of 4,4-dichloro-1,2-diazabuta-1,3-dienes. It was proven that this C–C bond-forming cascade reaction operates via an addition of trichloromethyl radical to the C═N bond of hydrazone followed by a base-induced elimination of HCl. The reaction was found to be very general, as diverse hydrazones possessing various aromatic groups at N-site, as well as aromatic, aliphatic, and heterocyclic substituents at C-site, are capable partners for coupling with a wide range of polyhalogenated compounds (CCl₃Br, CBr₄, CCl₃CN, CCl₃COOEt, CCl₃CF₃, CBr₃CF₃) to produce a family of functionalized 1,2-diazabuta-1,3-dienes. It was demonstrated that the prepared heterodienes are highly versatile building blocks for straightforward assembly of various valuable acyclic and heterocyclic molecules.