Coupling of Nonequivalent Aromatic Rings by Soluble Nickel Catalysts. A General Route to the 1,8-DiaryInaphthalene
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.
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.Additional details
- Eprint ID
- 60918
- Resolver ID
- CaltechAUTHORS:20151008-115813530
- NSF
- National Defense Education Act Fellow
- Centre National de la Recherche Scientifique (CNRS)
- Created
-
2015-10-10Created from EPrint's datestamp field
- Updated
-
2021-11-10Created from EPrint's last_modified field
- Other Numbering System Name
- Caltech Gates and Crellin Laboratories of Chemistry
- Other Numbering System Identifier
- 5122