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Coupling of Nonequivalent Aromatic Rings by Soluble Nickel Catalysts. A General Route to the 1,8-DiaryInaphthalene

Clough, Roger L. and Mison, Pierre and Roberts, John D. (1976) Coupling of Nonequivalent Aromatic Rings by Soluble Nickel Catalysts. A General Route to the 1,8-DiaryInaphthalene. Journal of Organic Chemistry, 41 (13). pp. 2252-2255. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20151008-115813530

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Abstract

A facile route to the l,&diarylnaphthalene derivatives is described. The parent compound, l,8-diphenylnaphthalene, can be prepared in two steps with 35% overall yield from the commercial 1,8-diaminonaphthalene. The key step in these preparations is the direct joining of two nonequivalent aromatic molecules by an organonickel-catalyzed Grignard-aryl halide coupling reaction at -15 ºC. The coupling reaction is regiospecific with respect to the position of substitution of both aromatic halves. The yields of thjs coupling reaction are high, even though the 1,8-diarylnaphthalenes are sterically crowded. The efficiency of the reaction under a variety of conditions is evaluated. The order of reactivity of aryl halides is found to be I > Br > Cl, and it is possible to effect coupling preferentially at an iodo group in the presence of a chloro group, the latter being available for further synthetic functionalization.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jo00875a006DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo00875a006PublisherArticle
Additional Information:© 1976 American Chemical Society. Received June 10, 1975. Supported by the National Science Foundation; (b) National Defense Education Act Fellow, 1971-1974; (c) CNRS Postdoctoral Fellow, 1971-1972.
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NSFUNSPECIFIED
National Defense Education Act FellowUNSPECIFIED
Centre National de la Recherche Scientifique (CNRS)UNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry5122
Issue or Number:13
Record Number:CaltechAUTHORS:20151008-115813530
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151008-115813530
Official Citation:Coupling of nonequivalent aromatic rings by soluble nickel catalysts. A general route to the 1,8-diarylnaphthalenes Roger L. Clough, Pierre Mison, and John D. Roberts The Journal of Organic Chemistry 1976 41 (13), 2252-2255 DOI: 10.1021/jo00875a006
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60918
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:10 Oct 2015 12:16
Last Modified:03 Oct 2019 09:02

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