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Dual Lewis Acid Promoted/Visible Light Driven Preparation of Aryl Diazenyl Oxazoles from Isocyanoacetamides and Arylazo Sulfones
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2024-11-01 , DOI: 10.1002/adsc.202401079 Enzo Delalande, Lorenzo Di Terlizzi, Camilla Russo, Carmine Volpe, Stefano Protti, mariateresa giustiniano
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2024-11-01 , DOI: 10.1002/adsc.202401079 Enzo Delalande, Lorenzo Di Terlizzi, Camilla Russo, Carmine Volpe, Stefano Protti, mariateresa giustiniano
While arylazo sulfones have been widely applied as arylating agents, their exploitation for diazenylation reactions has been previously limited to electron‐rich alkenes such as styrenes and silyl enol ethers. Herein we optimized a synthetic one‐pot protocol to access oxazolyl azo compounds via a selective domino ring‐closing/aryldiazenylation sequence by starting from arylazo sulfones and isocyanoacetamides in the presence of Sm(OTf)3 as the Lewis acid. The satisfactory substrate scope and functional group tolerance, along with scale‐up reaction both in batch and under continuous flow conditions provide a valuable approach to such a class of heteroaryl azo compounds.
中文翻译:
从异氰基乙酰胺和芳基氮化砜中制备芳基二氮卓二唑的双重路易斯酸促进/可见光驱动制备
虽然芳偶氮砜已广泛用作芳基化剂,但它们在二氮化反应中的利用以前仅限于富电子的烯烃,如苯乙烯和甲硅烯醇醚。在此,我们优化了一种合成的一锅法方案,通过在 Sm(OTf)3 作为路易斯酸存在下从芳偶氮砜和异氰基乙酰胺开始,通过选择性多米诺骨牌闭环/芳基二氮化序列获得恶唑酰偶氮化合物。令人满意的底物范围和官能团耐受性,以及分批和连续流条件下的放大反应,为这类杂芳基偶氮化合物提供了一种有价值的方法。
更新日期:2024-11-01
中文翻译:
从异氰基乙酰胺和芳基氮化砜中制备芳基二氮卓二唑的双重路易斯酸促进/可见光驱动制备
虽然芳偶氮砜已广泛用作芳基化剂,但它们在二氮化反应中的利用以前仅限于富电子的烯烃,如苯乙烯和甲硅烯醇醚。在此,我们优化了一种合成的一锅法方案,通过在 Sm(OTf)3 作为路易斯酸存在下从芳偶氮砜和异氰基乙酰胺开始,通过选择性多米诺骨牌闭环/芳基二氮化序列获得恶唑酰偶氮化合物。令人满意的底物范围和官能团耐受性,以及分批和连续流条件下的放大反应,为这类杂芳基偶氮化合物提供了一种有价值的方法。