Palladium-Catalyzed Carbonylative α-Arylation of tert-Butyl Cyanoacetate with (Hetero)aryl Bromides

The Journal of Organic Chemistry
Mikkel T JensenTroels Skrydstrup

Abstract

A three-component coupling protocol has been developed for the generation of 3-oxo-3-(hetero)arylpropanenitriles via a carbonylative palladium-catalyzed α-arylation of tert-butyl 2-cyanoacetates with (hetero)aryl bromides followed by an acid-mediated decarboxylation step. Through the combination of only a stoichiometric loading of carbon monoxide and mild basic reaction conditions such as MgCl2 and dicyclohexylmethylamine for the deprotonation step, an excellent functional group tolerance was ensured for the methodology. Through the use of (13)C-labeled carbon monoxide generated from (13)COgen, the corresponding (13)C-isotopically labeled β-ketonitriles were obtained, and these products could subsequently be converted into cyanoalkynes and 3-cyanobenzofurans with site specific (13)C-isotope labeling.

References

Mar 10, 2006·Organic Letters·Yaohui JiJames V Vowles
Dec 27, 2006·Bioorganic & Medicinal Chemistry Letters·Sunkyung LeeKyu Yang Yi
May 2, 2008·The Journal of Organic Chemistry·Zhenglai FangMark Cushman
Dec 20, 2013·Chemistry : a European Journal·Signe KorsagerTroels Skrydstrup
Jul 6, 2014·Chemistry : a European Journal·Johannes SchranckMatthias Beller
Dec 24, 2014·Organic & Biomolecular Chemistry·Ashenafi Damtew MamuyeVittorio Pace
Jan 31, 2015·Chemical Communications : Chem Comm·Zhong LianTroels Skrydstrup
Aug 4, 2015·Chemical Communications : Chem Comm·Guangwei RongXinfang Xu
Oct 24, 2015·Journal of the American Chemical Society·Ilya S MakarovTroels Skrydstrup

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Citations

Jun 3, 2018·Journal of Labelled Compounds & Radiopharmaceuticals·Dennis U NielsenTroels Skrydstrup
Nov 15, 2018·Molecular and Cellular Biochemistry·Chengmin HuangYuan Guo
Nov 15, 2017·Organic Letters·Thomas A ClohessyAllan J B Watson
Dec 16, 2020·The Journal of Organic Chemistry·Ge ZengRenhao Li

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