Single-flask preparation of polyazatriaryl ligands by sequential borylation/Suzuki–Miyaura coupling

✍ Scribed by Bertoldo Avitia; Eric MacIntosh; Samuel Muhia; Eric Kelson

• Book ID: 104098906
• Publisher: Elsevier Science
• Year: 2011
• Tongue: French
• Weight: 1012 KB
• Volume: 52
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2011.01.136

✦ Synopsis

We report a convenient single-flask methodology for the preparation of polyazatriaryl products with relevance to luminescence, catalysis, and pharmacology. The diborylation of 1,3-dibromobenzenes and double Suzuki-Miyaura coupling produces 1,3-diheteroarylbenzenes. Similarly, borylation of heteroaryl halides and double coupling to 2,6-dichloropyridine produces 2,6-diheteroarylpyridines. This methodology appears general in producing challenging polyheteroaryl targets as long as the boronic esters have no ortho heteroatoms and coupling avoids adjacent oxygens.