Sulfonate-Modified Picolinamide Diphosphine: A Ligand for Room-Temperature Palladium-Catalyzed Hydrocarboxylation in Water with High Branched Selectivity,ACS Catalysis

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Sulfonate-Modified Picolinamide Diphosphine: A Ligand for Room-Temperature Palladium-Catalyzed Hydrocarboxylation in Water with High Branched Selectivity
ACS Catalysis ( IF 11.3 ) Pub Date : 2023-09-19 , DOI: 10.1021/acscatal.3c03372
Ding Liu _{1,

2} , Tong Ru _{1,

2} , Zhixin Deng _{1,

2} , Luyun Zhang _{1,

2} , Yingtang Ning _{1,

2} , Fen-Er Chen _{1,

2,

3}

Affiliation

Alkyne hydrocarboxylation represents a powerful and industrially significant approach to α,β-unsaturated carboxylic acids. Herein, we report the development of a picolinamide-derived diphosphine ligand with a hydrophilic sulfonate (SO₃^–) group. The implementation of this ligand enabled the Pd-catalyzed hydrocarboxylation of alkynes at room temperature in water, allowing the reaction to proceed with various substrates in high yields and generally excellent branched selectivity. Further experimental and theoretical investigations highlight the role of ligand–metal cooperativity from basic pyridine and hydrophilic sulfonate in accelerating the key catalytic steps.

中文翻译：

磺酸盐改性吡啶酰胺二膦：室温钯催化水中高支化选择性加氢羧化的配体

炔烃加氢羧化代表了一种强大且具有工业意义的 α,β-不饱和羧酸方法。在此，我们报道了具有亲水性磺酸基（SO ₃^–）基团的吡啶酰胺衍生的二膦配体的开发。这种配体的应用使得钯催化的炔烃在室温下在水中进行加氢羧化成为可能，使得反应能够以高产率和优异的支化选择性与各种底物进行。进一步的实验和理论研究强调了碱性吡啶和亲水性磺酸盐的配体-金属协同作用在加速关键催化步骤中的作用。

更新日期：2023-09-19

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