TY - JOUR
T1 - A Vitamin B12 derivative catalyzed electrochemical trifluoromethylation and perfluoroalkylation of arenes and heteroarenes in organic media
AU - Hossain, Md Jakir
AU - Ono, Toshikazu
AU - Wakiya, Kosuke
AU - Hisaeda, Yoshio
N1 - Funding Information:
This work was supported by JST PRESTO Grant Number JPMJPR1414 and JSPS KAKENHI Grant Numbers JP16H04119 (Grant-in-Aid for Scientific Research (B) for Y. H.), JP16H01035 (Precisely Designed Catalysts with Customized Scaffolding for Y. H.), JP17H04875 (Grant-in-Aid for Young Scientists (A) for T. O.), and JP17H05161 (p-System Figuration for T. O.). We thank TOSOH F-TECH INC. for the gift of CF3I.
Publisher Copyright:
© 2017 The Royal Society of Chemistry.
PY - 2017
Y1 - 2017
N2 - The electrochemical trifluoromethylation and perfluoroalkylation of aromatic compounds mediated by a vitamin B12 derivative as a cobalt-based catalyst has been developed. The Co(i) species of a vitamin B12 derivative, prepared by controlled-potential electrolysis at -0.8 V vs. Ag/AgCl in methanol, reacted with RfI (Rf = CF3, n-C3F7, n-C4F9, n-C8F17, and n-C10F21) to form a Co-Rf complex. This complex released an Rf radical under visible light irradiation, which then reacted directly with non-activated (hetero)arenes to form the desired fluoroalkylated molecules through direct C-H functionalization. To our knowledge, this is the first report of a naturally derived vitamin B12 catalyzed trifluoromethylation and perfluoroalkylation of aromatic compounds as a cobalt-mediated catalyst.
AB - The electrochemical trifluoromethylation and perfluoroalkylation of aromatic compounds mediated by a vitamin B12 derivative as a cobalt-based catalyst has been developed. The Co(i) species of a vitamin B12 derivative, prepared by controlled-potential electrolysis at -0.8 V vs. Ag/AgCl in methanol, reacted with RfI (Rf = CF3, n-C3F7, n-C4F9, n-C8F17, and n-C10F21) to form a Co-Rf complex. This complex released an Rf radical under visible light irradiation, which then reacted directly with non-activated (hetero)arenes to form the desired fluoroalkylated molecules through direct C-H functionalization. To our knowledge, this is the first report of a naturally derived vitamin B12 catalyzed trifluoromethylation and perfluoroalkylation of aromatic compounds as a cobalt-mediated catalyst.
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U2 - 10.1039/c7cc06221d
DO - 10.1039/c7cc06221d
M3 - Article
C2 - 28929155
AN - SCOPUS:85030630703
SN - 1359-7345
VL - 53
SP - 10878
EP - 10881
JO - Chemical Communications
JF - Chemical Communications
IS - 79
ER -