Gold-catalyzed cycloisomerization of 1,6-diyne carbonates and esters to 2,4a-dihydro-1 H-fluorenes

Weidong Rao; Ming Joo Koh; Dan Li; Hajime Hirao; Philip Wai Hong Chan

doi:10.1021/ja4032727

Author(s)

Weidong Rao
Ming Joo Koh
Dan Li
Hajime Hirao
Philip Wai Hong Chan

Detail(s)

Original language	English
Pages (from-to)	7926-7932
Journal / Publication	Journal of the American Chemical Society
Volume	135
Issue number	21
Publication status	Published - 29 May 2013
Externally published	Yes

Link(s)

DOI	DOI https://doi.org/10.1021/ja4032727 Final Published version
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Link to Scopus	https://www.scopus.com/record/display.uri?eid=2-s2.0-84878413891&origin=recordpage
Permanent Link	https://scholars.cityu.edu.hk/en/publications/publication(17bdeb0b-771d-45da-8427-7a9d4e120977).html

Abstract

A synthetic method to prepare 2,4a-dihydro-1H-fluorenes efficiently from gold(I)-catalyzed 1,2-acyloxy migration/cyclopropenation/Nazarov cyclization of 1,6-diyne carbonates and esters is described. The suggested reaction pathway provides rare examples of [2,3]-sigmatropic rearrangement in this class of compounds as well as the involvement of an in situ formed cyclopropene intermediate in gold catalysis. Experimental and ONIOM(QM:QM′) [our own n-layered integrated molecular orbital and molecular mechanics(quantum mechanics:quantum mechanics′)] computational studies based on the proposed Au carbenoid species provide insight into this unique selectivity. © 2013 American Chemical Society.

Citation Format(s)

[ RIS ] [ BibTeX ]

Gold-catalyzed cycloisomerization of 1,6-diyne carbonates and esters to 2,4a-dihydro-1 H-fluorenes. / Rao, Weidong; Koh, Ming Joo; Li, Dan et al.

In: Journal of the American Chemical Society, Vol. 135, No. 21, 29.05.2013, p. 7926-7932.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62) › 21_Publication in refereed journal › peer-review

Rao, W, Koh, MJ, Li, D, Hirao, H & Chan, PWH 2013, 'Gold-catalyzed cycloisomerization of 1,6-diyne carbonates and esters to 2,4a-dihydro-1 H-fluorenes', Journal of the American Chemical Society, vol. 135, no. 21, pp. 7926-7932. https://doi.org/10.1021/ja4032727

Rao, W., Koh, M. J., Li, D., Hirao, H., & Chan, P. W. H. (2013). Gold-catalyzed cycloisomerization of 1,6-diyne carbonates and esters to 2,4a-dihydro-1 H-fluorenes. Journal of the American Chemical Society, 135(21), 7926-7932. https://doi.org/10.1021/ja4032727

Rao W, Koh MJ, Li D, Hirao H, Chan PWH. Gold-catalyzed cycloisomerization of 1,6-diyne carbonates and esters to 2,4a-dihydro-1 H-fluorenes. Journal of the American Chemical Society. 2013 May 29;135(21):7926-7932. doi: 10.1021/ja4032727

Rao, Weidong ; Koh, Ming Joo ; Li, Dan et al. / Gold-catalyzed cycloisomerization of 1,6-diyne carbonates and esters to 2,4a-dihydro-1 H-fluorenes. In: Journal of the American Chemical Society. 2013 ; Vol. 135, No. 21. pp. 7926-7932.