C–H Polyaddition of Dimethoxyarenes to Unconjugated Dienes by Rare Earth Catalysts

The C–H polyaddition of dimethoxyarenes such as 1,4-dimethoxybenzene and 4,4′-dimethoxybiphenyl to unconjugated dienes such as norbornadiene and 1,4-divinylbenzene has been achieved for the first time by using cationic half-sandwich rare earth alkyl catalysts. This protocol afforded novel polymer ma...

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Published inJournal of the American Chemical Society Vol. 138; no. 19; pp. 6147 - 6150
Main Authors Shi, Xiaochao, Nishiura, Masayoshi, Hou, Zhaomin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.05.2016
Amer Chemical Soc
Subjects
catalysts
chemical bonding
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
polymerization
polymers
Science & Technology
standard operating procedures
ACETOPHENONE
COMPLEXES
ALPHA,OMEGA-DIENES
ANISOLES
OLEFINS
BOND ACTIVATION
POLYMERIZATION
PYRIDINES
COPOLYMERIZATION
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Summary:The C–H polyaddition of dimethoxyarenes such as 1,4-dimethoxybenzene and 4,4′-dimethoxybiphenyl to unconjugated dienes such as norbornadiene and 1,4-divinylbenzene has been achieved for the first time by using cationic half-sandwich rare earth alkyl catalysts. This protocol afforded novel polymer materials consisting of dimethoxyarene moieties and nonpolar hydrocarbon structure motifs (cyclic, linear, and aromatic) in perfectly alternating sequences that are otherwise difficult to make. The reaction proceeded via CC double bond insertion into a C–H bond ortho to each of the two methoxy groups in a step-growth polymerization fashion.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.6b03859