Azidosubstituted arylboronic acids: synthesis and Suzuki–Miyaura cross-coupling reactions

Autor:	Andrei A. Vasil'ev, Sergey V. Shorshnev, Sergey I. Sviridov, Natalia L. Sergovskaya, Marina V. Chirskaya
Rok vydání:	2006
Předmět:	chemistry.chemical_compound Nitrile chemistry Aryl Organic Chemistry Drug Discovery Organic chemistry General Medicine Biochemistry Medicinal chemistry Coupling reaction
Zdroj:	Tetrahedron. 62:2639-2647
ISSN:	0040-4020
DOI:	10.1016/j.tet.2005.12.026
Popis:	Arylboronic acids having a remote azido group were prepared from the corresponding azidosubstituted aryl bromides via lithiation and treatment with trialkyl borates. Preparative yields were achieved when the starting aryl bromides possessed ortho-alkoxy groups, which would stabilize the intermediate aryllithium species. Conventional Suzuki cross-coupling of the arylboronic acids proceeded generally well with retention of azido group; however, sometimes azidomethyl fragment underwent oxidative transformation into a nitrile.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d2cb9da35b1f5b43f25ae6f6f9003c71 https://doi.org/10.1016/j.tet.2005.12.026 Zobrazit plný text záznamu Full Text from ScienceDirect