Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst

• Main Authors: Kimihiro Komeyama, Shunsuke Sakiyama, Kento Iwashita, Itaru Osaka, Ken Takaki
• Format: Article
• Language: English
• Published: Beilstein-Institut 2018-06-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: chromium; cobalt; diastereoselective; homoallyl alcohols; hybrid catalyst; three-component coupling
• Online Access: https://doi.org/10.3762/bjoc.14.118
• ISSN: 1860-5397

The cobalt/chromium-catalyzed three-component coupling of aryl iodides, allenes, and aldehydes has been developed to afford multi-substituted homoallylic alcohols in a diastereoselective manner. Control experiments for understanding the reaction mechanism reveal that the cobalt catalyst is involved in the oxidative addition and carbometalation steps in the reaction, whereas the chromium salt generates highly nucleophilic allylchromium intermediates from allylcobalt species, without the loss of stereochemical information, to allow the addition to aldehydes.