Synthesis of multisubstituted pyrroles by nickel-catalyzed arylative cyclizations of N-tosyl alkynamides†,Chemical Communications

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Synthesis of multisubstituted pyrroles by nickel-catalyzed arylative cyclizations of N-tosyl alkynamides†
Chemical Communications ( IF 4.3 ) Pub Date : 2018-09-22 00:00:00 , DOI: 10.1039/c8cc06649c
Simone M. Gillbard _{1,

2,

3,

4,

5} , Chieh-Hsu Chung _{1,

2,

3,

4,

5} , Somnath Narayan Karad _{1,

2,

3,

4,

5} , Heena Panchal _{1,

2,

3,

4,

5} , William Lewis _{2,

5,

6,

7,

8} , Hon Wai Lam _{1,

2,

3,

4,

5}

Affiliation

The synthesis of multisubstituted pyrroles by the nickel-catalyzed reaction of N-tosyl alkynamides with arylboronic acids is reported. These reactions are triggered by alkyne arylnickelation, followed by cyclization of the resulting alkenylnickel species onto the amide. The reversible E/Z isomerization of the alkenylnickel species is critical for cyclization. This method was applied to the synthesis of pyrroles that are precursors to BODIPY derivatives and a biologically active compound.

中文翻译：

由镍-催化的环化arylative吡咯多取代的合成Ñ -tosyl alkynamides †

报道了通过N-甲苯磺酰基炔基酰胺与芳基硼酸的镍催化反应合成多取代的吡咯。这些反应是由炔烃基芳基镍化反应触发，然后将所得的烯基镍基化合物环化到酰胺上。烯基镍物种的可逆E / Z异构化对于环化至关重要。该方法用于合成作为BODIPY衍生物和生物活性化合物的前体的吡咯。

更新日期：2018-09-22

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