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. doi:10.1021/jo00875a006. https://resolver.caltech.edu/CaltechAUTHORS:20151008-115813530
Full text is not posted in this repository. Consult Related URLs below.
Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20151008-115813530
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: |
| |||||||||
| 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. | |||||||||
| Funders: |
| |||||||||
| Other Numbering System: |
| |||||||||
| Issue or Number: | 13 | |||||||||
| DOI: | 10.1021/jo00875a006 | |||||||||
| 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: | 10 Nov 2021 22:41 |
Repository Staff Only: item control page
