TY - JOUR
T1 - Palladium-Catalyzed Tandem Ester Dance/Decarbonylative Coupling Reactions
AU - Kubo, Masayuki
AU - Inayama, Naomi
AU - Ota, Eisuke
AU - Yamaguchi, Junichiro
PY - 2022/6/3
Y1 - 2022/6/3
N2 - "Dance reaction" on the aromatic ring is a powerful method in organic chemistry to translocate functional groups on arene scaffolds. Notably, dance reactions of halides and pseudohalides offer a unique platform for the divergent synthesis of substituted (hetero)aromatic compounds when combined with transition-metal-catalyzed coupling reactions. Herein, we report a tandem reaction of ester dance and decarbonylative coupling enabled by palladium catalysis. In this reaction, 1,2-translocation of the ester moiety on the aromatic ring is followed by decarbonylative coupling with nucleophiles to enable the installation of a variety of nucleophiles at the position adjacent to the ester in the starting material.
AB - "Dance reaction" on the aromatic ring is a powerful method in organic chemistry to translocate functional groups on arene scaffolds. Notably, dance reactions of halides and pseudohalides offer a unique platform for the divergent synthesis of substituted (hetero)aromatic compounds when combined with transition-metal-catalyzed coupling reactions. Herein, we report a tandem reaction of ester dance and decarbonylative coupling enabled by palladium catalysis. In this reaction, 1,2-translocation of the ester moiety on the aromatic ring is followed by decarbonylative coupling with nucleophiles to enable the installation of a variety of nucleophiles at the position adjacent to the ester in the starting material.
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U2 - 10.1021/acs.orglett.2c01432
DO - 10.1021/acs.orglett.2c01432
M3 - Article
C2 - 35604648
AN - SCOPUS:85131271028
SN - 1523-7060
VL - 24
SP - 3855
EP - 3860
JO - Organic Letters
JF - Organic Letters
IS - 21
ER -