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Tellurium-mediated cycloaromatization of acyclic enediynes under mild conditions.

Author
Abstract
:

The cycloaromatization of acyclic enediynes typically requires very high temperatures (>160 degrees C) and dilute conditions to proceed in a synthetically useful yield. These conditions hinder reaction throughput, inhibiting the use of this reaction for the large-scale production of materials. The reaction of sodium telluride with acyclic arenediynes yields the corresponding tellurepine, which under gentle heating extrudes Te degrees to yield the cycloaromatization product. We have developed conditions that form sodium telluride from inexpensive tellurium metal in situ, and that also perform the desilylation of silylated arenediynes in the same process. Under our conditions, we are able to perform desilylation and cycloaromatization at temperatures as low as 40 degrees C and on a scale as large as 5 g in standard laboratory glassware.

Year of Publication
:
2004
Journal
:
Journal of the American Chemical Society
Volume
:
126
Issue
:
5
Number of Pages
:
1338-9
Date Published
:
2004
ISSN Number
:
0002-7863
URL
:
https://doi.org/10.1021/ja0389467
DOI
:
10.1021/ja0389467
Short Title
:
J Am Chem Soc
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