Cross-Coupling of Alkyl Redox-Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis
Cross-Coupling of Alkyl Redox-Active Esters with Benzophenone Imines: Tandem Photoredox and Copper Catalysis
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DOI：
10.1002/anie.201804873
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发表时间：
2018-07-20
影响因子：
16.6
通讯作者：
Hu, Xile
中科院分区：
文献类型：
--
作者：
Mao, Runze;Balon, Jonathan;Hu, Xile
烷基胺是一类重要的有机化合物，在医药和材料化学中具有重要的应用价值。到目前为止，通过金属催化的烷基亲电试剂与氮亲核试剂的交叉偶联来合成烷基胺的方法非常少。本文描述了一种采用串联光氧化还原和铜催化以使容易衍生自烷基羧酸的烷基N-羟基邻苯二甲酰亚胺酯与二苯甲酮衍生的亚胺交叉偶联的方法。偶联产物的水解提供烷基化伯胺。伯、仲和叔烷基基团可以被转移，并且偶联容许不同的官能团集合。该方法允许天然产物和药物的快速官能化，并且可以用于加速从容易获得的化学原料合成药物。
Alkyl amines are an important class of organic compounds in medicinal and materials chemistry. Until now very have been very few methods for the synthesis of alkyl amines by metal-catalyzed cross-coupling of alkyl electrophiles with nitrogen nucleophiles. Described here is an approach to employ tandem photoredox and copper catalysis to enable the cross-coupling of alkyl N-hydroxyphthalimide esters, readily derived from alkyl carboxylic acids, with benzophenone-derived imines. Hydrolysis of the coupling products furnish alkylated primary amines. Primary, secondary, and tertiary alkyl groups can be transferred, and the coupling tolerates a diverse set of functional groups. The method allows rapid functionalization of natural products and drugs, and can be used to expedite syntheses of pharmaceuticals from readily available chemical feedstocks.