Decarboxylative Tribromination for the Selective Synthesis of Tribromomethyl Ketone and Tribromovinyl Derivatives,Advanced Synthesis & Catalysis

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Decarboxylative Tribromination for the Selective Synthesis of Tribromomethyl Ketone and Tribromovinyl Derivatives
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-09-04 , DOI: 10.1002/adsc.201800851
Aravindan Jayaraman ₁ , Eunjeong Cho ₁ , Jimin Kim ₁ , Sunwoo Lee ₁

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Tribromomethyl ketone and tribromovinyl derivatives were selectively prepared from the decarboxylative tribromination. The reaction between propiolic acid derivatives and dibromoisocyanuric acid (DBCA)/H₂O afforded predominantly a tribromomethyl ketone derivative in the presence of AgOAc (10 mol%). When the same reaction was conducted with 2,2,6,6‐tetramethyl‐1‐piperidinyloxy (TEMPO) instead of AgOAc, tribromovinyl derivatives were exclusively formed in good yields. It was found that ethynyl bromide is an intermediate.

中文翻译：

脱羧三溴化反应选择性合成三溴甲基酮和三溴乙烯基衍生物

由脱羧三溴化作用选择性地制备三溴甲基酮和三溴乙烯基衍生物。在AgOAc（10mol％）存在下，丙酸衍生物与二溴异氰尿酸（DBCA）/ H ₂ O之间的反应主要得到三溴甲基酮衍生物。当用2,2,6,6-四甲基-1-哌啶基氧基（TEMPO）代替AgOAc进行相同的反应时，仅以高收率形成了三溴乙烯基衍生物。发现乙炔基溴是中间体。

更新日期：2018-09-04

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