Nickel-Catalyzed Asymmetric Cross-Couplings of Racemic Propargylic Halides with Arylzinc Reagents

• Published in: Journal of the American Chemical Society Vol. 130; no. 38; pp. 12645 - 12647
• Main Authors: Smith, Sean W, Fu, Gregory C
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 24.09.2008; Amer Chemical Soc
• Subjects: Alkynes - chemical synthesis; Alkynes - chemistry; Benzene Derivatives - chemical synthesis; Benzene Derivatives - chemistry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Folic Acid Antagonists - chemical synthesis; Folic Acid Antagonists - pharmacology; Nickel - chemistry; Organometallic Compounds - chemistry; Pargyline - analogs & derivatives; Pargyline - chemistry; Physical Sciences; Science & Technology; Tetrahydrofolate Dehydrogenase - chemistry; Tetrahydrofolate Dehydrogenase - metabolism; Zinc - chemistry; IODOALKANES
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja805165y

A stereoconvergent method for the catalytic asymmetric Negishi cross-coupling of racemic secondary propargylic halides with arylzinc reagents has been developed. Neither family of compounds has previously been shown to be a suitable partner in such coupling processes. From a practical point of view, it is noteworthy that the catalyst components (NiCl2·glyme and pybox ligand 1) are commercially available.