Visible-light-induced phenylchalcogenyl-oxygenation of allenes having aryl or electron withdrawing substituents with ambient air as a sole oxidant
Visible-light-induced phenylchalcogenyl-oxygenation of allenes having aryl or electron withdrawing substituents with ambient air as a sole oxidant
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DOI：
10.1039/c6ob02033j
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发表时间：
2016-01-01
影响因子：
3.2
通讯作者：
Narayanarao, Vykunthapu
中科院分区：
文献类型：
--
作者：
Kumaraswamy, Gullapalli;Vijaykumar, Swargam;Narayanarao, Vykunthapu
以活化的烯烃为原料，合成了区域和立体选择性取代芳基的α，β-不饱和醛和酮。这种温和的非金属氧化完全由良性的环境空气驱动，并由可见光触发。相同的原料在理想的厌氧条件下生成了不含氧产物的2，3-二苯基硒加合物，证明了溶解氧是两条不同反应途径的化学开关。该方案的显著特点是通过照射两个有机分子中的一个来实现单电子转移(SET)，从而避免使用增敏剂来形成自由基离子对。
The synthesis of regio-and stereoselective aryl substituted alpha, beta-unsaturated aldehydes and ketones from activated allenes was achieved. This mild and non-metallic oxidation is exclusively driven by benign ambient air and triggered by visible light. The same starting materials under ideal anaerobic conditions led to the 2,3-diphenylselenation adduct with no trace of oxygenated products, demonstrating dissolved oxygen as a chemical switch for two different reaction pathways. The salient feature of this protocol is the single electron transfer (SET) achieved by irradiation of one of two organic molecules thereby avoiding a sensitizer to form a radical ion pair.