onr:"swepub:oai:gup.ub.gu.se/257882"
Search: onr:"swepub:oai:gup.ub.gu.se/257882" > Manganese-Catalyzed...
- 1 of 1
- Previous record
- Next record
- To hitlist
Manganese-Catalyzed Cross-Coupling of Aryl Halides and Grignard Reagents by a Radical Mechanism
- Antonacci, G. (author)
- Ahlburg, A. (author)
- Fristrup, P. (author)
- show more...
- Madsen, R. (author)
- show less...
- (creator_code:org_t)
- 2017-08-25
- 2017
- English.
- In: European Journal of Organic Chemistry. - : Wiley. - 1434-193X. ; :32, s. 4758-4764
- Journal article (peer-reviewed)
Abstract
Subject headings
Close
- The substrate scope and the mechanism have been investigated for the MnCl2-catalyzed cross-coupling reaction between aryl halides and Grignard reagents. The transformation proceeds rapidly and in good yield when the aryl halide component is an aryl chloride containing a cyano or an ester group in the para position or a cyano group in the ortho position. A range of other substituents gave no conversion of the aryl halide or led to the formation of side products. A broader scope was observed for the Grignard reagents, where a variety of alkyl- and arylmagnesium chlorides participated in the coupling. Two radical-clock experiments were carried out, and in both cases an intermediate aryl radical was successfully trapped. The cross-coupling reaction is therefore believed to proceed by an S(RN)1 mechanism, with a triorganomanganate complex serving as the most likely nucleophile and single-electron donor. Other mechanistic scenarios were excluded based on the substrate scope of the aryl halide.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- Cross-coupling
- Grignard reagents
- Manganese
- Radical reactions
- Reaction mechanisms
- Earth-
- nucleophilic-substitution reactions
- electron-transfer
- organomagnesium
- reagents
- anion-radicals
- iodides
- chlorobenzonitriles
- reduction
- complexes
- ethers
- Chemistry
Publication and Content Type
- ref (subject category)
- art (subject category)
Find in a library
- European Journal of Organic Chemistry (Search for host publication in LIBRIS)
To the university's database
- 1 of 1
- Previous record
- Next record
- To hitlist
Find more in SwePub
- By the author/editor
- Antonacci, G.
- Ahlburg, A.
- Fristrup, P.
- Norrby, Per-Ola, ...
- Madsen, R.
- About the subject
-
- NATURAL SCIENCES
- NATURAL SCIENCES
- and Chemical Science ...
- and Organic Chemistr ...
- Articles in the publication
- European Journal ...
- By the university
- University of Gothenburg
Search outside SwePub
- Extend your search to:
- Google Book Search
- Google Scholar
Kungliga biblioteket hanterar dina personuppgifter i enlighet med EU:s dataskyddsförordning (2018), GDPR. Läs mer om hur det funkar här.
Så här hanterar KB dina uppgifter vid användning av denna tjänst.
- Copyright © LIBRIS - National Library Systems
- LIBRIS.kb.se
