TY - JOUR
T1 - Transition-Metal-Free Intermolecular Hydrocarbonation of Styrenes Mediated by NaH/1,10-Phenanthroline
AU - Nozawa-Kumada, Kanako
AU - Onuma, So
AU - Ono, Kanako
AU - Kumagai, Tomohiro
AU - Iwakawa, Yuki
AU - Sato, Katsuhiko
AU - Shigeno, Masanori
AU - Kondo, Yoshinori
N1 - Funding Information:
This work was financially supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI Grant no. 19H03346 and 21K06470. This work was also supported by Takeda Science Foundation, the Iwatani Naoji Foundation, Ube Corporation Foundation, the Kurata Grants from The Hitachi Global Foundation, the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED), and Tohoku University Center for Gender Equality Promotion (TUMUG) Support Project.
Publisher Copyright:
© 2023 Wiley-VCH GmbH.
PY - 2023
Y1 - 2023
N2 - A transition-metal-free intermolecular coupling reaction of halocompounds with styrenes in the presence of NaH and 1,10-phenanthroline was developed. This reaction afforded hydrocarbonated products with complete anti-Markovnikov selectivity. The method allows the use of a wide range of halocompounds, including aryl and alkyl halides, and good functional group tolerance. Detailed mechanistic studies indicated that an anilide anion generated in situ by the NaH-mediated reduction of 1,10-phenanthroline works as an electron donor and a hydrogen source.
AB - A transition-metal-free intermolecular coupling reaction of halocompounds with styrenes in the presence of NaH and 1,10-phenanthroline was developed. This reaction afforded hydrocarbonated products with complete anti-Markovnikov selectivity. The method allows the use of a wide range of halocompounds, including aryl and alkyl halides, and good functional group tolerance. Detailed mechanistic studies indicated that an anilide anion generated in situ by the NaH-mediated reduction of 1,10-phenanthroline works as an electron donor and a hydrogen source.
KW - carboradical
KW - hydrocarbonation
KW - single-electron-transfer
KW - sodium hydride
KW - styrenes
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U2 - 10.1002/chem.202203143
DO - 10.1002/chem.202203143
M3 - Article
AN - SCOPUS:85149014087
SN - 0947-6539
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
ER -