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Metal‐Free Synthesis of 3‐Arylquinolin‐2‐ones from N ,2‐Diaryl‐ acrylamides via Phenyliodine(III) Bis(2,2‐dimethylpropanoate)‐ Mediated Direct Oxidative C−C Bond Formation
Author(s) -
Cao Yang,
Zhao Hui,
ZhangNegrerie Daisy,
Du Yunfei,
Zhao Kang
Publication year - 2016
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.201600512
Subject(s) - chemistry , annulation , boron trifluoride , oxidative phosphorylation , oxindole , medicinal chemistry , stereochemistry , boron , combinatorial chemistry , organic chemistry , catalysis , biochemistry
Treatment of N ,2‐diarylacrylamides with the organoiodine(III) compound phenyliodine(III) bis(2,2‐dimethylpropanoate) [PhI(O 2 C‐ t‐ Bu) 2 ] and boron trifluoride etherate (BF 3 ⋅Et 2 O) resulted in a direct and selective oxidative C( sp 2 )−C( sp 2 ) bond formation leading to a convenient assemblage, under mild conditions, of the biologically important 3‐arylquinolin‐2‐one skeleton. Differing from the five‐membered oxindole products from oxidative cyclizations mediated by transition metals, this metal‐free approach realized a direct annulation of the N ‐arylacrylamide into a six‐membered 3‐arylquinolin‐2‐one skeleton.