TY - JOUR
T1 - Aryl Dance Reaction of Arylbenzoheteroles
AU - Nakahara, Hikaru
AU - Yamaguchi, Junichiro
N1 - Funding Information:
This work was supported by JSPS KAKENHI Grant JP21H05213 and JST ERATO Grant JPMJER1901 (to J.Y.). The authors thank Dr. Kenta Kato (Waseda University) for assistance with X-ray crystallography. The Materials Characterization Central Laboratory of Waseda University is acknowledged for the support of HRMS measurement.
Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/11/4
Y1 - 2022/11/4
N2 - We report a 1,2-migration (aryl dance reaction) of the aryl group on heteroles. AlCl3can efficiently convert C3-arylheteroles to C2-arylheteroles. Depending on the electron density of the substrate, conversion from C2- to C3-arylheteroles was also possible with catalytic Zn(OTf)2. A one-pot aryl dance/acylation or bromination and arylation/aryl dance cascade was also demonstrated.
AB - We report a 1,2-migration (aryl dance reaction) of the aryl group on heteroles. AlCl3can efficiently convert C3-arylheteroles to C2-arylheteroles. Depending on the electron density of the substrate, conversion from C2- to C3-arylheteroles was also possible with catalytic Zn(OTf)2. A one-pot aryl dance/acylation or bromination and arylation/aryl dance cascade was also demonstrated.
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U2 - 10.1021/acs.orglett.2c03442
DO - 10.1021/acs.orglett.2c03442
M3 - Article
C2 - 36286610
AN - SCOPUS:85140965372
SN - 1523-7060
VL - 24
SP - 8083
EP - 8087
JO - Organic Letters
JF - Organic Letters
IS - 43
ER -