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Well-Defined Pre-Catalysts in Amide and Ester Bond Activation

Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND 58108–6050, USA
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Academic Editor: Michal Szostak
Molecules 2019, 24(2), 215; https://doi.org/10.3390/molecules24020215
Received: 3 December 2018 / Revised: 2 January 2019 / Accepted: 2 January 2019 / Published: 9 January 2019
(This article belongs to the Special Issue Amide Bond Activation)

Abstract

Over the past few decades, transition metal catalysis has witnessed a rapid and extensive development. The discovery and development of cross-coupling reactions is considered to be one of the most important advancements in the field of organic synthesis. The design and synthesis of well-defined and bench-stable transition metal pre-catalysts provide a significant improvement over the current catalytic systems in cross-coupling reactions, avoiding excess use of expensive ligands and harsh conditions for the synthesis of pharmaceuticals, agrochemicals and materials. Among various well-defined pre-catalysts, the use of Pd(II)-NHC, particularly, provided new avenues to expand the scope of cross-coupling reactions incorporating unreactive electrophiles, such as amides and esters. The strong σ-donation and tunable steric bulk of NHC ligands in Pd-NHC complexes facilitate oxidative addition and reductive elimination steps enabling the cross-coupling of broad range of amides and esters using facile conditions contrary to the arduous conditions employed under traditional catalytic conditions. Owing to the favorable catalytic activity of Pd-NHC catalysts, a tremendous progress was made in their utilization for cross-coupling reactions via selective acyl C–X (X=N, O) bond cleavage. This review highlights the recent advances made in the utilization of well-defined pre-catalysts for C–C and C–N bond forming reactions via selective amide and ester bond cleavage. View Full-Text
Keywords: pre-catalysts; palladium catalysis; amide bond activation; ester bond activation; cross-coupling pre-catalysts; palladium catalysis; amide bond activation; ester bond activation; cross-coupling
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Vemula, S.R.; Chhoun, M.R.; Cook, G.R. Well-Defined Pre-Catalysts in Amide and Ester Bond Activation. Molecules 2019, 24, 215.

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