Premium
Rhodium(III)‐ and Iridium(III)‐Catalyzed C7 Alkylation of Indolines with Diazo Compounds
Author(s) -
Ai Wen,
Yang Xueyan,
Wu Yunxiang,
Wang Xuan,
Li Yuanchao,
Yang Yaxi,
Zhou Bing
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405077
Subject(s) - diazo , alkylation , rhodium , iridium , regioselectivity , chemistry , catalysis , intermolecular force , substrate (aquarium) , medicinal chemistry , combinatorial chemistry , organic chemistry , molecule , oceanography , geology
A Rh III ‐catalyzed procedure for the C7‐selective CH alkylation of various indolines with α‐diazo compounds at room temperature is reported. The advantages of this process are: 1) simple, mild, and pH‐neutral reaction conditions, 2) broad substrate scope, 3) complete regioselectivity, 4) no need for an external oxidant, and 5) N 2 as the sole byproduct. Furthermore, alkylation and bis‐alkylation of carbazoles at the C1 and C8 positions have also been developed. More significantly, for the first time, a successful Ir III ‐catalyzed intermolecular insertion of arene CH bonds into α‐diazo compounds is reported.