Ni-Catalyzed Photochemial Sulfamidation of Aryl Chlorides with Soluble Organic Amine as Base,Organometallics

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Ni-Catalyzed Photochemial Sulfamidation of Aryl Chlorides with Soluble Organic Amine as Base
Organometallics ( IF 2.5 ) Pub Date : 2024-02-26 , DOI: 10.1021/acs.organomet.3c00506
Geyang Song ₁ , Jiameng Song ₁ , Jianyang Dong ₁ , Gang Li ₁ , Juan Fan ₁ , Dong Xue ₁

Affiliation

Transition-metal-catalyzed sulfonamidation is an attractive approach for the synthesis of N-(hetero)aryl sulfonamides, which are present in many bioactive pharmaceuticals. However, most catalyst systems require the use of strongly basic alkoxide salts as base, which leads to problems of functional group compatibility and a lack of selectivity for sulfonamides containing multiple NH₂ groups. Here, we reported the Ni-catalyzed photochemical C–N coupling of (hetero)aryl chlorides with sulfonamides using mild organic amines as base without the addition of external photocatalyst. This Ni-catalyzed C–N coupling features a broad substrate scope (84 examples), excellent functional group tolerance, and high sulfonamide group selectivity. The utility of this approach in synthetic chemistry is demonstrated by the late-stage functionalization or synthesis of pharmaceutical molecules.

中文翻译：

可溶性有机胺基镍催化芳基氯光化学磺酰胺化反应

过渡金属催化的磺酰胺化是合成N- (杂)芳基磺酰胺的一种有吸引力的方法，N-(杂)芳基磺酰胺存在于许多生物活性药物中。然而，大多数催化剂体系需要使用强碱性醇盐作为碱，这导致官能团相容性问题以及对含有多个NH ₂基团的磺酰胺缺乏选择性。在这里，我们报道了使用温和的有机胺作为碱，在不添加外部光催化剂的情况下，镍催化（杂）芳基氯与磺酰胺的光化学C-N偶联。这种镍催化的 C-N 偶联具有广泛的底物范围（84 个实例）、出色的官能团耐受性和高磺酰胺基选择性。药物分子的后期功能化或合成证明了这种方法在合成化学中的实用性。

更新日期：2024-02-26

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