Intermolecular oxyarylation of olefins with aryl halides and TEMPOH catalyzed by the phenolate anion under visible light,Chemical Science

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Intermolecular oxyarylation of olefins with aryl halides and TEMPOH catalyzed by the phenolate anion under visible light
Chemical Science ( IF 7.6 ) Pub Date : 2020-06-04 , DOI: 10.1039/d0sc02160a
Kangjiang Liang _{1,

2,

3,

4,

5} , Qian Liu _{1,

2,

3,

4,

5} , Lei Shen _{1,

2,

3,

4,

5} , Xipan Li _{1,

2,

3,

4,

5} , Delian Wei _{1,

2,

3,

4,

5} , Liyan Zheng _{1,

2,

3,

4,

5} , Chengfeng Xia _{1,

2,

3,

4,

5}

Affiliation

The phenolate anion was discovered as a new photocatalyst with strong reduction potentials. Under visible light irradiation, the phenolate anion enabled the reduction of (hetero)aryl halides (including electron-rich aryl chlorides) to (hetero)aryl radicals through single electron transfer. Based on this new photocatalyst, a novel and efficient photocatalytic protocol for the intermolecular oxyarylation of olefins with aryl halides and TEMPOH was developed. The developed three-component coupling reaction proceeded under redox-neutral reaction conditions with stable and readily available synthons and exhibited broad substrate scope. The utility of this process was further highlighted by the diversified chemical manipulation of the resulting oxyarylation products and the late-stage modification of active pharmaceutical ingredients.

中文翻译：

苯酚阴离子在可见光下催化烯烃与芳基卤化物和TEMPOH的分子间氧化氧化

酚盐阴离子被发现是一种具有强大还原潜力的新型光催化剂。在可见光照射下，酚酸根阴离子能够通过单电子转移将（杂）芳基卤化物（包括富电子的芳基氯化物）还原为（杂）芳基基团。基于这种新的光催化剂，开发了一种新颖且有效的光催化方案，用于烯烃与芳基卤化物和TEMPOH的分子间氧化。所开发的三组分偶联反应是在氧化还原中性反应条件下，以稳定且易于获得的合成子进行的，并显示了广泛的底物范围。通过对所得的氧化芳基化产物进行多样化的化学处理以及对活性药物成分进行后期修饰，进一步突出了该方法的实用性。

更新日期：2020-07-15

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