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Facile Assembly of Benzo[ b ]naphtho[2,3‐ d ]azocin‐6(5 H )‐ones by a Palladium‐Catalyzed Double Carbometalation
Author(s) -
Gong Xinxing,
Chen Mo,
Yao Liangqing,
Wu Jie
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201600211
Subject(s) - palladium , cyclobutanone , catalysis , chemistry , ring (chemistry) , selectivity , combinatorial chemistry , functional group , medicinal chemistry , transformation (genetics) , stereochemistry , organic chemistry , polymer , biochemistry , gene
The palladium‐catalyzed reaction of 2‐alkynylanilines with 2‐(2‐bromobenzylidene)cyclobutanone as an efficient route to 7,8‐dihydrobenzo[ b ]naphtho[2,3‐ d ]azocin‐6(5 H )‐ones was developed. The fused eight‐membered ring was constructed conveniently. During the reaction process, double carbometalation was involved, which resulted in excellent selectivity with the formation of three new bonds. This transformation is highly efficient and leads to fused polycycles in good to excellent yields with good functional group tolerance.