Application of Palladium Based Precatalytic Systems in the Suzuki‐Miyaura Cross‐Coupling Reactions of Chloro‐ Heterocycles

• Published in: ChemistrySelect (Weinheim) 2020-08, Vol.5 (29), p.9005-9016
• Main Authors: Bhaskaran, Savitha, Padusha, M. Syed Ali, Sajith, Ayyiliath M
• Format: Article
• Language: English
• Subjects: Chloro heterocycles; Palladium; Phosphine Ligands; Precatalysts; Suzuki-Miyaura coupling
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.202002357

Carbon‐Carbon bond forming reactions using Suzuki‐Miyaura cross‐coupling (SMC) technology to construct aryl‐aryl, aryl‐heteroaryl or heteroaryl‐heteroaryl linkages continues to play a vital role in pharmaceuticals, agrochemicals, material science and manufacturing fields. The importance of Suzuki‐Miyaura cross‐coupling which is also reflected in their use in industrial applications, warrants the development of highly efficient catalytic systems that allows the cross‐coupling of economically attractive heteroaryl chlorides. Conversely, the low reactivity of heteroaryl chlorides followed by problems associated with multi‐heteroatom systems amplifies the difficulties involved in SMC procedures. This review focuses on the developments made in the palladium mediated SMC of chloro heterocycles using various palladium/Ligand combinations and highlights the significant improvements achieved by the use of Buchwald's palladium precatalysts. Cross‐coupling reactions of chloro heterocycles The facile synthesis of challenging multi‐heteroatom containing architectures using Suzuki‐Miyaura cross‐coupling strategy from inexpensive and atom‐economical heteroaryl chlorides is highlighted. Catalytic trends which involves the development of several demanding phosphine ligands and also the significant improvements achieved by the use of palladium precatalyts is reviewed.