Four‐Component Synthesis of Phosphonium Salts: Application Toward an Alternative Approach to Cross‐Coupling for the Synthesis of Bis‐Heteroarenes

• Published in: Angewandte Chemie International Edition Vol. 56; no. 18; pp. 5106 - 5110
• Main Authors: Chen, Yi‐Ru, Reddy, Ganapuram Madhusudhan, Hong, Shao‐Hao, Wang, Ying‐Zheng, Yu, Jhen‐Kuei, Lin, Wenwei
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 24.04.2017; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Aromatic compounds; bis-heteroarenes; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Coupling; Cross coupling; multicomponent reactions; organophosphonium salts; Phosphine; Physical Sciences; Salts; Science & Technology; Wittig reactions; multicomponent reactions; INTRAMOLECULAR WITTIG REACTIONS; Wittig reactions; ACYL CHLORIDES; bis-heteroarenes; VERSATILE; FUNCTIONAL BENZOFURANS; ARENES; cross-coupling; REACTIVITY; organophosphonium salts; INDOLES
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201700945

A series of stable phosphonium salts have been synthesized via a novel four‐component reaction of an arene nucleophile, 2‐heteroatom substituted aryl aldehyde, and phosphine in presence of an acid. The phosphonium salts thus obtained were utilized for the synthesis of a variety of bis‐heteroarenes, providing an efficient alternative method to the classical cross‐coupling strategies. Connect four: A four‐component reaction for the generation of an array of phosphonium salts has been demonstrated. The generated salts were applied for the synthesis of bis‐heteroarenes, thereby promising an efficient alternative to the classical cross‐coupling strategies.