Premium
Rh III ‐Catalyzed C–H Allylation of Amides and Domino Cycling Synthesis of 3,4‐Dihydroisoquinolin‐1(2 H )‐ones with N ‐Bromosuccinimide
Author(s) -
Dai Huimin,
Yu Chao,
Lu Changsheng,
Yan Hong
Publication year - 2016
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.201501551
Subject(s) - chemistry , catalysis , medicinal chemistry , aniline , intramolecular force , amide , bromide , domino , n bromosuccinimide , vinyl bromide , ether , organic chemistry , halogenation
Abstract A Rh III ‐catalyzed C–H allylation of electron‐deficient arenes, heteroarenes, and alkenes at room temperature was developed with allyl bromide. The reaction was carried out in diethyl ether without dehydration, and C–H activation was assisted by the directing anionic nitrogen of the aniline‐derived amide. Following the allylation, a domino cycling synthesis of 3,4‐dihydroisoquinolin‐1(2 H )‐ones with N ‐bromosuccinimide (NBS) through intramolecular aminobromination of the introduced double bond was achieved.