Iron-catalyzed cascade addition/cyclization of 2-biphenyl isocyanides with toluenes: a highly efficient approach to 6-benzylated phenanthridines

A highly efficient Fe-catalyzed cascade addition/cyclization of 2-biphenyl isocyanides with toluenes for the synthesis of 6-benzylated phenanthridines has been reported. Di-tert-butyl peroxide (DTBP) was employed as both a radical initiator and an oxidant. The procedure tolerates various functional...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018-11, Vol.16 (45), p.8837-8844
Main Authors: Wang, Liping, Xiong, Weikang, Peng, Yiyuan, Ding, Qiuping
Format: Article
Language:English
Subjects:
Biphenyl
Functional groups
Iron
NMR
Nuclear magnetic resonance
Peroxide
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Summary:A highly efficient Fe-catalyzed cascade addition/cyclization of 2-biphenyl isocyanides with toluenes for the synthesis of 6-benzylated phenanthridines has been reported. Di-tert-butyl peroxide (DTBP) was employed as both a radical initiator and an oxidant. The procedure tolerates various functional groups, providing the corresponding products in moderate to good yields. The proposed mechanism involves the cascade addition of benzyl radicals to the isocyanides and the following radical aromatic cyclization.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02462f