Display options
Cite
Pati K, Michas C, Allenger D, et al. Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization. J Org Chem. 2015;80(23):11706-17doi: 10.1021/acs.joc.5b01014.
Pati, K., Michas, C., Allenger, D., Piskun, I., Coutros, P. S., Gomes, G. d. o. s. . P., & Alabugin, I. V. (2015). Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization. The Journal of organic chemistry, 80(23), 11706-17. https://doi.org/10.1021/acs.joc.5b01014
Pati, Kamalkishore, et al. "Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization." The Journal of organic chemistry vol. 80,23 (2015): 11706-17. doi: https://doi.org/10.1021/acs.joc.5b01014
Pati K, Michas C, Allenger D, Piskun I, Coutros PS, Gomes Gdos P, Alabugin IV. Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization. J Org Chem. 2015 Dec 04;80(23):11706-17. doi: 10.1021/acs.joc.5b01014. Epub 2015 Aug 14. PMID: 26248062.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2015 Dec 04;80(23):11706-17. doi: 10.1021/acs.joc.5b01014. Epub 2015 Aug 14.

Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization.

The Journal of organic chemistry

Kamalkishore Pati, Christopher Michas, David Allenger, Ilya Piskun, Peter S Coutros, Gabriel Dos Passos Gomes, Igor V Alabugin

Affiliations

  1. Department of Chemistry and Biochemistry, Florida State University , Tallahassee, Florida 32306, United States.

PMID: 26248062 DOI: 10.1021/acs.joc.5b01014

Abstract

The majority of Sn-mediated cyclizations are reductive and, thus, cannot give a fully conjugated product. This is a limitation in the application of Sn-mediated radical cascades for the preparation of fully conjugated molecules. In this work, we report an oxidatively terminated Bu3Sn-mediated cyclization of an alkyne where AIBN, the commonly used initiator, takes on a new function as an oxidative agent. Sn-mediated radical transformation of biphenyl aryl acetylenes into functionalized phenanthrenyl stannanes can be initiated via two potentially equilibrating vinyl radicals, one of which can be trapped by the fast 6-endoclosure at the biphenyl moiety in good to excellent yields. The efficient preparation of Sn-substituted phenanthrenes opens access to convenient building blocks for the construction of larger polyaromatics.

Publication Types