Catalytic C–C coupling of diazo compounds with arylboronic acids: using surface modified sewage sludge as catalyst,Green Chemistry

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Catalytic C–C coupling of diazo compounds with arylboronic acids: using surface modified sewage sludge as catalyst
Green Chemistry ( IF 9.3 ) Pub Date : 2020-04-27 , DOI: 10.1039/d0gc00317d
Zhipeng Zhang _{1,

2,

3,

4,

5} , Yang Yu _{4,

6,

7,

8,

9} , Yuxing Xie _{4,

5,

8,

10} , Timothy Hughes _{9,

11,

12,

13} , Jun Xu _{4,

14,

15} , Fei Huang _{4,

5,

8,

10} , He Huang _{1,

2,

3,

4,

5}

Affiliation

A green, mild and efficient synthesis of diarylmethines using sewage sludge-derived carbonaceous materials (SW) by perchloric acid catalyzed coupling reactions between diazo compounds and arylboronic acids was developed. The reaction shows a high level of functional tolerance and a broad substrate scope. Furthermore, the highly selective 1,2-alkyl shift products were furnished through the sterically demanding R⁴, R⁵ migration of diazo compounds (3-diazochromanone). The structures of 1,2-shift products have been further confirmed by single-crystal X-ray analysis. Significantly, the synthesis of the core structures of darifenacin (a clinical drug for overactive bladder syndrome, OAB) and diclofensine (a stimulant drug showing antidepressant and monoamine reuptake inhibitor activity) further demonstrated the efficacy and synthetic potential of this method.

中文翻译：

重氮化合物与芳基硼酸的催化性CC偶联：以表面改性的污水污泥为催化剂

通过高氯酸催化重氮化合物与芳基硼酸之间的偶联反应，开发了一种绿色，温和且高效的合成方法，该方法利用污水污泥衍生的碳质材料（SW）合成二芳基次甲基。该反应显示出高水平的功能耐受性和广泛的底物范围。此外，通过空间要求高的R ⁴，R ⁵提供了高选择性的1,2-烷基转移产物重氮化合物（3-重氮苯并二氢吡喃酮）的迁移。通过单晶X射线分析进一步证实了1，2-移位产物的结构。值得注意的是，darifenacin（一种用于膀胱过度活动症的临床药物，OAB）和diclofensine（一种显示出抗抑郁和单胺再摄取抑制剂活性的兴奋剂）的核心结构的合成进一步证明了该方法的有效性和合成潜力。

更新日期：2020-07-06

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