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Tandem, Catalyst‐Free C‐C Synthesis of Nitriles from Aldehydes and Methyl Cyanoacetate with Sodium Hypophosphite
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-11-19 , DOI: 10.1002/ejoc.202401108 Vasily Korochantsev, Artemy Fatkulin, Evgeniya Podyacheva, Alexander Boldyrev, Oleg Afanasyev, Denis Chusov
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-11-19 , DOI: 10.1002/ejoc.202401108 Vasily Korochantsev, Artemy Fatkulin, Evgeniya Podyacheva, Alexander Boldyrev, Oleg Afanasyev, Denis Chusov
Saturated carbon chain elongation is a common refrain in numerous synthetic pathways. While the formation of C‐C single bonds is of primary importance in organic synthesis, simultaneous introduction of functional groups such as nitrile or ester can reasonably increase its practical utility to prepare multifunctional products. Knoevenagel reaction is one of the powerful tools to create carbon backbones of organic molecules; however, it requires subsequent reduction and/or decarboxylation to achieve a product with a saturated carbon chain. Herein we report a convenient one‐step protocol for the reductive condensation between methyl cyanoacetate and aldehydes in the presence of stable, ecologically benign, cheap and available in bulk amounts sodium hypophosphite as a reductant. A description of both the reaction capabilities and limitations is given in this paper.
中文翻译:
用次磷酸钠从醛和氰乙酸甲酯串联、无催化剂的 C-C 合成丁腈
饱和碳链伸长是许多合成途径中的常见术语。虽然 C-C 单键的形成在有机合成中至关重要,但同时引入腈或酯等官能团可以合理地增加其制备多功能产品的实际实用性。Knoevenagel 反应是产生有机分子碳主链的有力工具之一;然而,它需要随后的还原和/或脱羧才能获得具有饱和碳链的产品。在此,我们报告了一种方便的一步法方案,用于在稳定、生态无害、廉价且大量次磷酸钠作为还原剂存在的情况下,氰乙酸甲酯和醛之间的还原缩合。本文对反应能力和局限性进行了描述。
更新日期:2024-11-19
中文翻译:
用次磷酸钠从醛和氰乙酸甲酯串联、无催化剂的 C-C 合成丁腈
饱和碳链伸长是许多合成途径中的常见术语。虽然 C-C 单键的形成在有机合成中至关重要,但同时引入腈或酯等官能团可以合理地增加其制备多功能产品的实际实用性。Knoevenagel 反应是产生有机分子碳主链的有力工具之一;然而,它需要随后的还原和/或脱羧才能获得具有饱和碳链的产品。在此,我们报告了一种方便的一步法方案,用于在稳定、生态无害、廉价且大量次磷酸钠作为还原剂存在的情况下,氰乙酸甲酯和醛之间的还原缩合。本文对反应能力和局限性进行了描述。