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Ramakrishna TV, Sharp PR. Naphthalenes, isoquinolines, and a benzazocine from zirconocene-copper-mediated coupling of benzocyclobutadiene with nitriles and alkynes. Org Lett. 2003;5(6):877-9doi: 10.1021/ol034040u.
Ramakrishna, T. V., & Sharp, P. R. (2003). Naphthalenes, isoquinolines, and a benzazocine from zirconocene-copper-mediated coupling of benzocyclobutadiene with nitriles and alkynes. Organic letters, 5(6), 877-9. https://doi.org/10.1021/ol034040u
Ramakrishna, T V V, and Sharp, Paul R. "Naphthalenes, isoquinolines, and a benzazocine from zirconocene-copper-mediated coupling of benzocyclobutadiene with nitriles and alkynes." Organic letters vol. 5,6 (2003): 877-9. doi: https://doi.org/10.1021/ol034040u
Ramakrishna TV, Sharp PR. Naphthalenes, isoquinolines, and a benzazocine from zirconocene-copper-mediated coupling of benzocyclobutadiene with nitriles and alkynes. Org Lett. 2003 Mar 20;5(6):877-9. doi: 10.1021/ol034040u. PMID: 12633095.
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Org Lett. 2003 Mar 20;5(6):877-9. doi: 10.1021/ol034040u.

Naphthalenes, isoquinolines, and a benzazocine from zirconocene-copper-mediated coupling of benzocyclobutadiene with nitriles and alkynes.

Organic letters

T V V Ramakrishna, Paul R Sharp

Affiliations

  1. Department of Chemistry, University of Missouri-Columbia, Columbia, Missouri 65211, USA.

PMID: 12633095 DOI: 10.1021/ol034040u

Abstract

[reaction: see text] Commercially available 1-bromobenzocyclobutene is a potentially useful synthon particularly with the application of organometallic methodology. Here we show that it is readily converted into Cp(2)Zr(benzocyclobutadiene), which couples with alkynes or nitriles giving five-membered zirconacycles. Treatment of these alkyne- or nitrile-derived zirconacycles with CuCl yields substituted naphthalenes, isoquinolines, or in the presence of MeO(2)C-CC-CO(2)Me, a 3-benzazocine containing an eight-membered ring [corrected].

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