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Synfacts 2020; 16(12): 1434
DOI: 10.1055/s-0040-1719552
Metals in Synthesis

Copper-Catalyzed C–N Cross-Coupling of Sterically Hindered Aryl Halides and Amines

Contributor(s):
Mark Lautens
,
Austin D. Marchese
Modak A, Nett AJ, Swift EC, Haibach MC, Chan VS, Franczyk TS, Shekhar S, *, Cook SP. * Indiana University, Bloomington and AbbVie Inc., North Chicago, USA
Cu-Catalyzed C–N Coupling with Sterically Hindered Partners.

ACS Catal. 2020;
10: 10495-10499
DOI: 10.1021/acscatal.0c02965
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Key words

copper catalysis - C–N coupling - sterical hindrance

Significance

The Cook and Shekhar groups report a copper-catalyzed C–N cross-coupling reaction of bulky (di-)ortho-substituted aryl iodides and sterically encumbered amines. A variety of alkyl and aryl amines with a wide pK a range were successfully employed in the reaction. The authors propose either a highly electron-rich or anionic Cu(I) catalyst is generated, facilitating the difficult oxidative addition process.


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Comment

The pyrrole-ol class of ligands were identified via high-throughput screening of a compound library from AbbVie. The benzyl group on the ligand is proposed to increase the stability of the ligand, while the CF3 group was found to be essential for the reactivity. The Hantzsch ester was added as a reductant which is proposed to increase the catalyst lifetime. Furthermore, the addition of molecular sieves was found to reduce the extent of side-product formation.


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Publication History

Article published online:
17 November 2020

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