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Iron‐Catalyzed exo ‐Selective Synthesis of Cyanoalkyl Indolines via Cyanoisopropylarylation of Unactivated Alkenes
Author(s) -
Li Yanni,
Chang Yu,
Li Yufen,
Cao Cheng,
Yang Jinshuang,
Wang Baoling,
Liang Deqiang
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800296
Subject(s) - chemistry , moiety , azobisisobutyronitrile , selectivity , nitrile , catalysis , radical initiator , polymer chemistry , combinatorial chemistry , organic chemistry , polymer , polymerization
An iron‐catalyzed cyanoalkylation using azobisisobutyronitrile (AIBN) is reported. With unactivated double bond as the radical acceptor, N ‐allyl anilines underwent cyanoisopropylation/cyclization cascade to afford 3‐cyanoalkyl indolines bearing a tertiary nitrile moiety, which were otherwise unavailable. Excellent exo ‐selectivity was always observed, and such a selectivity and the unusual performance of the iron catalyst might be related to the metal bridging between the radical and the substrate.