Distal Amidoketone Synthesis Enabled by Dimethyl Benziodoxoles via Dual Copper/Photoredox Catalysis,ACS Catalysis

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Distal Amidoketone Synthesis Enabled by Dimethyl Benziodoxoles via Dual Copper/Photoredox Catalysis
ACS Catalysis ( IF 11.3 ) Pub Date : 2023-03-02 , DOI: 10.1021/acscatal.3c00230
Yuanyuan Ge ₁ , Yingbo Shao _{2,

3} , Shuang Wu _{1,

4} , Pan Liu _{1,

5} , Junzhao Li ₁ , Hanzhang Qin _{1,

6} , Yanxia Zhang ₇ , Xiao-song Xue _{2,

6} , Yiyun Chen _{1,

4,

6}

Affiliation

Herein, we report distal amidoketone and nitrogen-functionalized ketone syntheses from alcohols and N–H nucleophiles enabled by hypervalent iodine dimethyl benziodoxoles, BI^m. Dimethyl benziodoxoles BI^m dually activate alcohols and various N–H nucleophiles by forming key BI^m–O and BI^m–N complexes in which the BI^m–N complex is characterized by X-ray crystallography and computationally investigated. Readily available N–H nucleophile imides, sulfonamides, carbamates, triazoles, indazoles, and sulfoximines engage in photoredox/copper catalysis to synthesize distal amidoketones and nitrogen-functionalized ketones with excellent regioselectivity and chemoselectivity. This reaction scales up to grams, applies to late-stage complex molecule modification, and streamlines synthetic routes.

中文翻译：

Dimethyl Benziodoxoles 通过双铜/光氧化还原催化合成远端氨基酮

^{在此，我们报告了由高价碘二甲基苯并氧醇 (BI m} ) 启用的醇和 N-H 亲核试剂合成的远端氨基酮和氮功能化酮。二甲基苯并氧唑 BI ^m通过形成关键的 BI ^m –O 和 BI ^m –N 复合物来双重激活醇和各种 N-H 亲核试剂，其中 BI ^m–N 络合物的特征在于 X 射线晶体学和计算研究。现成的 N-H 亲核试剂酰亚胺、磺酰胺、氨基甲酸酯、三唑、吲唑和亚砜亚胺参与光氧化还原/铜催化，以合成具有出色区域选择性和化学选择性的远端酰胺酮和氮功能化酮。该反应可放大至克级，适用于后期复杂分子修饰，并简化合成路线。

更新日期：2023-03-02

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