Halogen Bond (XB) Promoted α‑Tribromomethylation of N‑Aryltetrahydroisoquinolines and Further Cyclization to 5,6-Dihydroindolo[2,1‑a]isoquinolines

Halogen Bond (XB) Promoted α‑Tribromomethylation of N‑Aryltetrahydroisoquinolines and Further Cyclization to 5,6-Dihydroindolo[2,1‑a]isoquinolines

Using CBr4 as a halogen bond donor and the source of tribromomethyl group, a halogen bond promoted tribromomethylation of N-aryltetrahydroisoquinolines was achieved. This reaction was also extended to the construction of the dibenzopyrrocoline alkaloid skeleton through a one-pot process. The mechani...

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Veröffentlicht in:Journal of organic chemistry 2023-08, Vol.88 (15), p.11310-11321
Hauptverfasser: Li, Yuemei, Zhang, Shuwei, Ding, Han, Sun, Zheng, Ma, Qiyuan, Yuan, Yu, Jia, Xiaodong
Format: Artikel
Sprache:eng
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Zusammenfassung:Using CBr4 as a halogen bond donor and the source of tribromomethyl group, a halogen bond promoted tribromomethylation of N-aryltetrahydroisoquinolines was achieved. This reaction was also extended to the construction of the dibenzopyrrocoline alkaloid skeleton through a one-pot process. The mechanistic study confirmed the existence of the halogen bond.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00861