Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross-Coupling

Autor:	Chung‐Yang Huang, Abigail G. Doyle
Rok vydání:	2015
Předmět:	Olefin fiber Chemistry Negishi coupling Ligand Phenethylamines General Chemistry Biochemistry Combinatorial chemistry Catalysis Reductive elimination Colloid and Surface Chemistry Coupling (computer programming) Organic chemistry Chemoselectivity
Zdroj:	Journal of the American Chemical Society. 137:5638-5641
ISSN:	1520-5126 0002-7863
DOI:	10.1021/jacs.5b02503
Popis:	A Ni-catalyzed Negishi cross-coupling with 1,1-disubstituted styrenyl aziridines has been developed. This method delivers valuable β-substituted phenethylamines via a challenging reductive elimination that affords a quaternary carbon. A novel electron-deficient olefin ligand, Fro-DO, proved crucial for achieving high rates and chemoselectivity for C-C bond formation over β-H elimination. This ligand is easy to access, is stable, and presents a modular framework for reaction discovery and optimization. We expect that these attributes, combined with the fact that the ligands impart distinct electronic properties to a metal, will support the invention of new transformations not previously possible using established ligands.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::cffbf460cbbad76634f9dac5c63c27d7 https://doi.org/10.1021/jacs.5b02503 Zobrazit plný text záznamu