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Free‐Amine‐Directed Alkenylation of C(sp 2 )H and Cycloamination by Palladium Catalysis
Author(s) -
Liang Zunjun,
Ju Long,
Xie Yongju,
Huang Lehao,
Zhang Yuhong
Publication year - 2012
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.201202672
Subject(s) - hydroamination , amine gas treating , regioselectivity , palladium , chemistry , catalysis , medicinal chemistry , alkyl , aryl , ring (chemistry) , organic chemistry
A new protocol for the palladium‐catalyzed free‐amine‐directed alkenylation of C(sp 2 )H bonds and cycloamination is described. Substituted biaryl‐2‐amines react with various alkenes, including electron‐deficient alkenes, aryl alkenes and alkyl alkenes, to give the corresponding phenanthridines with exclusive regioselectivity. The use of α‐branched styrenes leads to the formation of tricyclic compounds with a seven‐membered amine ring. The method operates through a free‐amine‐directed alkenylation and a subsequent hydroamination cyclization reaction.