Evaluating 1,1′-Bis(phosphino)ferrocene Ancillary Ligand Variants in the Nickel-Catalyzed C–N Cross-Coupling of (Hetero)aryl Chlorides
| Autor: | Jillian S. K. Clark, Michael J. Ferguson, Christopher N. Voth, Mark Stradiotto |
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| Rok vydání: | 2017 |
| Předmět: |
Indole test
Trifluoromethyl 010405 organic chemistry Ligand Furfurylamine Aryl Organic Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry 3. Good health 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound chemistry Ferrocene Morpholine Electrophile Organic chemistry Physical and Theoretical Chemistry |
| Zdroj: | Organometallics. 36:679-686 |
| ISSN: | 1520-6041 0276-7333 |
| Popis: | Previous reports in the literature have established the utility of 1,1′-bis(diphenylphosphino)ferrocene (DPPF, LPh) in the nickel-catalyzed cross-coupling of (hetero)aryl electrophiles with primary or secondary amines. In an effort to evaluate the effect of varying the PR2-donor groups on catalytic performance in such transformations, a series of 10 structurally varied 1,1′-bis(bis(alkyl/aryl)phosphino)ferrocene ancillary ligands (LX) were systematically examined in selected competitive test cross-couplings of (hetero)aryl halides with furfurylamine, morpholine, and indole employing Ni(COD)2/LX catalyst mixtures. In addition to the excellent performance observed for the parent ligand LPh in a number of the test transformations explored, selected dialkylphosphino (e.g., DiPPF, LiPr) and meta-disubstituted diarylphosphino variants of LPh also proved highly effective. In particular, the electron-deficient ligand variant LCF3 featuring 3,5-bis(trifluoromethyl)phenyl groups on phosphorus was found to exhibit s... |
| Databáze: | OpenAIRE |
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