Cargando…
Sequential olefination–dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard or zinc reagent
Products of main group elements from cross-coupling reactions have been shown to serve as Lewis acids, mediating further reactions of organic coupling products. Thus, the nickel-catalysed olefination of benzylic dithioacetal with MeMgI in benzene in a sealed Schlenk tube at 130 °C generates magnesiu...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8959447/ https://www.ncbi.nlm.nih.gov/pubmed/35424913 http://dx.doi.org/10.1039/d2ra00841f |
_version_ | 1784677156081631232 |
---|---|
author | Yu, Lei Lai, Guo-Qiao Zhang, Pinglu Li, Ze Luh, Tien-Yau |
author_facet | Yu, Lei Lai, Guo-Qiao Zhang, Pinglu Li, Ze Luh, Tien-Yau |
author_sort | Yu, Lei |
collection | PubMed |
description | Products of main group elements from cross-coupling reactions have been shown to serve as Lewis acids, mediating further reactions of organic coupling products. Thus, the nickel-catalysed olefination of benzylic dithioacetal with MeMgI in benzene in a sealed Schlenk tube at 130 °C generates magnesium mercaptide which regioselectively converts 2-arylpropene into a dimer in good yield. Aryl iodide reacts with 2-propenylmagnesium bromide in the presence of 1,2-ethanedithiol and NiCl(2)(PPh(3))(2) to yield the same dimer. Replacement of the Grignard reagent by an organozinc reagent gives the dimers in a better yield. |
format | Online Article Text |
id | pubmed-8959447 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-89594472022-04-13 Sequential olefination–dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard or zinc reagent Yu, Lei Lai, Guo-Qiao Zhang, Pinglu Li, Ze Luh, Tien-Yau RSC Adv Chemistry Products of main group elements from cross-coupling reactions have been shown to serve as Lewis acids, mediating further reactions of organic coupling products. Thus, the nickel-catalysed olefination of benzylic dithioacetal with MeMgI in benzene in a sealed Schlenk tube at 130 °C generates magnesium mercaptide which regioselectively converts 2-arylpropene into a dimer in good yield. Aryl iodide reacts with 2-propenylmagnesium bromide in the presence of 1,2-ethanedithiol and NiCl(2)(PPh(3))(2) to yield the same dimer. Replacement of the Grignard reagent by an organozinc reagent gives the dimers in a better yield. The Royal Society of Chemistry 2022-03-28 /pmc/articles/PMC8959447/ /pubmed/35424913 http://dx.doi.org/10.1039/d2ra00841f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Yu, Lei Lai, Guo-Qiao Zhang, Pinglu Li, Ze Luh, Tien-Yau Sequential olefination–dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard or zinc reagent |
title | Sequential olefination–dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard or zinc reagent |
title_full | Sequential olefination–dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard or zinc reagent |
title_fullStr | Sequential olefination–dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard or zinc reagent |
title_full_unstemmed | Sequential olefination–dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard or zinc reagent |
title_short | Sequential olefination–dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard or zinc reagent |
title_sort | sequential olefination–dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl grignard or zinc reagent |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8959447/ https://www.ncbi.nlm.nih.gov/pubmed/35424913 http://dx.doi.org/10.1039/d2ra00841f |
work_keys_str_mv | AT yulei sequentialolefinationdimerisationofbenzylicdithioacetalsbythenickelcatalysedreactionwithmethylgrignardorzincreagent AT laiguoqiao sequentialolefinationdimerisationofbenzylicdithioacetalsbythenickelcatalysedreactionwithmethylgrignardorzincreagent AT zhangpinglu sequentialolefinationdimerisationofbenzylicdithioacetalsbythenickelcatalysedreactionwithmethylgrignardorzincreagent AT lize sequentialolefinationdimerisationofbenzylicdithioacetalsbythenickelcatalysedreactionwithmethylgrignardorzincreagent AT luhtienyau sequentialolefinationdimerisationofbenzylicdithioacetalsbythenickelcatalysedreactionwithmethylgrignardorzincreagent |