TY - JOUR
T1 - Selective Synthesis of Pyrano[3,2- b]indoles or Cyclopenta[ b]indoles Tethered with Medium-Sized Rings via Cascade C-C σ-Bond Cleavage and C-H Functionalization
AU - Wang, Mengdan
AU - Yang, Yajie
AU - Yin, Liqiang
AU - Feng, Ye
AU - Li, Yanzhong
N1 - Publisher Copyright:
©
PY - 2021/1/1
Y1 - 2021/1/1
N2 - Highly atom-economical tandem reactions have been developed for the synthesis of pyrano[3,2-b]indoles or cyclopenta[b]indoles tethered with 7-, 8-, or 9-membered rings. These reactions first undergo a carbon-carbon σ-bond cleavage reaction of cyclic β-ketoesters. Next, in the presence of CuCl2 and Ag2CO3, intramolecular O-H/C-H coupling occurs to give pyrano[3,2-b]indoles. This is the first example for capture of the enoloxyl radical of the intramolecular C-O bond formation reaction, whereas C3 nucleophilic addition afforded cyclopenta[b]indoles using TsOH·H2O.
AB - Highly atom-economical tandem reactions have been developed for the synthesis of pyrano[3,2-b]indoles or cyclopenta[b]indoles tethered with 7-, 8-, or 9-membered rings. These reactions first undergo a carbon-carbon σ-bond cleavage reaction of cyclic β-ketoesters. Next, in the presence of CuCl2 and Ag2CO3, intramolecular O-H/C-H coupling occurs to give pyrano[3,2-b]indoles. This is the first example for capture of the enoloxyl radical of the intramolecular C-O bond formation reaction, whereas C3 nucleophilic addition afforded cyclopenta[b]indoles using TsOH·H2O.
UR - https://www.scopus.com/pages/publications/85099158812
U2 - 10.1021/acs.joc.0c02310
DO - 10.1021/acs.joc.0c02310
M3 - 文章
AN - SCOPUS:85099158812
SN - 0022-3263
VL - 86
SP - 683
EP - 692
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 1
ER -