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Synthesis of 8‐Oxoberbines and Related Benzolactams by Pd(OAc) 2 ‐Catalyzed Direct Aromatic Carbonylation
Author(s) -
Miyazawa Mamoru,
Tokuhashi Takashi,
Horibata Akiyoshi,
Nakamura Takatoshi,
Onozaki Yu,
Kurono Nobuhito,
Senboku Hisanori,
Tokuda Masao,
Ohkuma Takeshi,
Orito Kazuhiko
Publication year - 2013
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.1044
Subject(s) - chemistry , carbonylation , catalysis , medicinal chemistry , selectivity , phosphine , palladium , alkoxy group , organic chemistry , carbon monoxide , alkyl
A variety of alkoxy‐substituted benzolactams with a berbine or yohimbane skeleton were prepared from 1‐benzyl‐1,2,3,4‐tetrahydroisoquinolines or 1‐benzyl‐1,2,3,4‐tetrahydro‐β‐carbolines by a phosphine‐free Pd(II)‐catalyzed direct aromatic carbonylation in a Pd(OAc) 2 ‐Cu(OAc) 2 catalytic system. The site selectivity was compared with that of the carbonylation with Pd(OAc) 2 or Pd(OAc) 2 ·2 PPh 3 , respectively.