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Aromatic C–H Addition to Ketones: The Effect of Directing Groups
Author(s) -
Zhang XiSha,
Zhu QiLei,
Luo FeiXian,
Chen Guihua,
Wang Xin,
Shi ZhangJie
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301115
Subject(s) - chemistry , intermolecular force , steric effects , rhodium , reactivity (psychology) , catalysis , quinoline , hydrogen bond , transition metal , medicinal chemistry , substrate (aquarium) , organic chemistry , molecule , medicine , oceanography , alternative medicine , pathology , geology
Abstract The first example of the transition‐metal‐catalyzed direct intermolecular C–H bond addition to ketones was achieved by using a rhodium catalyst. A significant influence of the directing group on the reactivity was observed, and sterically more hindered directing groups could promote the reaction. In addition, intermolecular hydrogen bonding played a role in stabilizing the product. The substrate scope for the quinoline derivatives was very good.