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Liberation of acrylates from nickelalactones via Ni─O ring opening with alkyl iodides
Author(s) -
Zhang Zhizhi,
Guo Fangjie,
Kühn Fritz E.,
Sun Jing,
Zhou Mingdong,
Fang Xiangchen
Publication year - 2017
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3567
Subject(s) - chemistry , reagent , acrylate , alkylation , alkyl , bond cleavage , acrylic acid , ring (chemistry) , polymer chemistry , organic chemistry , catalysis , copolymer , polymer
The utilization of carbon dioxide as a feedstock for the production of raw chemicals is of high current industrial interest. One attractive reaction is the transformation of carbon dioxide into acrylic acid or acrylates. The cleavage of the Ni─O bond of nickelalactones may result in the formation of acrylates. In this work, C 2 H 5 I, CF 3 CH 2 I and CF 3 I are studied as alkylation reagents for the Ni─O ring opening of nickelalactones. The results indicate that both C 2 H 5 I and CF 3 CH 2 I are able to release acrylates from nickelalactones. Based on the experimental evidence and literature precedents, a mechanism – proceeding via Ni─O ring opening of nickelalactone, β‐H elimination to release the acrylate and reductive elimination for recovery of the Ni(0) species – is proposed.