Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2,Organic Letters

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Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2
Organic Letters ( IF 4.9 ) Pub Date : 2021-06-07 , DOI: 10.1021/acs.orglett.1c01503
Akira Shiozuka ₁ , Kohei Sekine _{1,

2} , Yoichiro Kuninobu _{1,

2}

Affiliation

Herein, direct unreactive C–N borylation of aromatic amines by a photocatalyst was achieved. The C–N borylation of aromatic amines with bis(pinacolato)diboron (B₂pin₂) proceeded using a pyrene catalyst under light irradiation to afford desired borylated products and aminoborane as a byproduct. The yield of the borylated product improved under a CO₂ atmosphere which probably reduced the inhibitory effect of aminoborane. Mechanistic studies suggested that the C–N bond cleavage and C–B bond formation proceeded via a concerted pathway.

中文翻译：

CO ₂增强非反应性芳香胺的光诱导脱氨基硼酰化

在此，通过光催化剂实现了芳香胺的直接非反应性 C-N 硼化。芳香胺与双（频哪醇）二硼（B ₂ pin ₂）的 C-N 硼化反应使用芘催化剂在光照射下进行，得到所需的硼化产物和氨基硼烷作为副产物。在CO ₂气氛下硼酸化产物的产率提高，这可能降低了氨基硼烷的抑制作用。机理研究表明，C-N 键断裂和 C-B 键形成是通过协同途径进行的。

更新日期：2021-06-18

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