Bibliographic Details
| Title: |
Triphenyiphosphine-Mediated Reductive Cyclization of 2-Nitrobiphenyls: A Practical and Convenient Synthesis of Carbazoles. |
| Authors: |
Freeman, Adam W.1 adam.freeman@kodak.com, Urvoy, Marie1, Criswell, Megan E.1 |
| Source: |
Journal of Organic Chemistry. 6/24/2005, Vol. 70 Issue 13, p5014-5019. 6p. 4 Diagrams, 3 Charts. |
| Subjects: |
Solvents, Solution (Chemistry), Organic chemistry, Chemical reactions, Ring formation (Chemistry) |
| Abstract: |
The synthesis of a series of substituted carbazoles from the corresponding 2-nitrobiphenyl derivatives using a novel modification of the Cadogan reaction is described. Cyclization of the 2-nitrobiphenyls was achieved via reductive deoxygenation of the nitro groups using a slight excess of triphenylphosphine in a suitable solvent. We have observed a temperature dependence on the extent of conversion under these conditions, with higher boiling solvents affording higher yields across a range of substrates. The new reaction conditions are very straightforward and convenient to execute, tolerate a broad range of functional groups, and yield carbazole products in the absence of unwanted side products. [ABSTRACT FROM AUTHOR] |
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| Database: |
Engineering Source |
