Details

Autor(en) / Beteiligte

• Crockett, Michael P
• Tyrol, Chet C
• Wong, Alexander S
• Li, Bo
• Byers, Jeffery A

Titel

Iron-Catalyzed Suzuki–Miyaura Cross-Coupling Reactions between Alkyl Halides and Unactivated Arylboronic Esters

Ist Teil von

• Organic letters, 2018-09, Vol.20 (17), p.5233-5237

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2018

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• An iron-catalyzed cross-coupling reaction between alkyl halides and arylboronic esters was developed that does not involve activation of the boronic ester with alkyllithium reagents nor requires magnesium additives. A combination of experimental and theoretical investigations revealed that lithium amide bases coupled with iron complexes containing deprotonated cyanobis­(oxazoline) ligands were best to obtain high yields (up to 89%) in catalytic cross-coupling reactions. Mechanistic investigations implicate carbon-centered radical intermediates and highlight the critical importance of avoiding conditions that lead to iron aggregates. The new iron-catalyzed Suzuki–Miyaura reaction was applied toward the shortest reported synthesis of the pharmaceutical Cinacalcet.