Saalfrank RW, Haubner M, Deutscher C, Bauer W, Clark T (1999)
Publication Status: Published
Publication Type: Journal article
Publication year: 1999
Publisher: American Chemical Society
Book Volume: 64
Pages Range: 6166-6168
Journal Issue: 17
Reaction of(2-bromophenylethynyl)trimethylsilane 1 with trimethyl berate yielded the alkynearyl-boronic acid 2, which was coupled in situ with the bromoallenes 3 to give enyne-allenes 4. The intermediates 4 underwent a spontaneous cation-mediated C-2-C-7 cycloaromatization with a concomitant 1,2-shift of the trimethylsilyl group to give the naphthalene derivatives 5. Besides 5, yne-allenes 10 were isolated by chromatography of the crude reaction products. A key step in the formation of 10 is the hydrolysis of the aryl boronic acid 2, which led to phenylethynyltrimethylsilane 8. Under the reaction conditions used, the TMS group of 8 was subsequently removed to give phenylacetylene 9, which further reacted with the bromoallenes 3 to furnish the yne-allenes 10.
APA:
Saalfrank, R.W., Haubner, M., Deutscher, C., Bauer, W., & Clark, T. (1999). Cation-mediated, substituent-controlled, C-2-C-7 cycloaromatization of an enyne-allene. Journal of Organic Chemistry, 64(17), 6166-6168.
MLA:
Saalfrank, Rolf W., et al. "Cation-mediated, substituent-controlled, C-2-C-7 cycloaromatization of an enyne-allene." Journal of Organic Chemistry 64.17 (1999): 6166-6168.
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