Display options
Cite
Mackey K, Pardo LM, Prendergast AM, et al. Cyclization of 4-Phenoxy-2-coumarins and 2-Pyrones via a Double C-H Activation. Org Lett. 2016;18(11):2540-3doi: 10.1021/acs.orglett.6b00751.
Mackey, K., Pardo, L. M., Prendergast, A. M., Nolan, M. T., Bateman, L. M., & McGlacken, G. P. (2016). Cyclization of 4-Phenoxy-2-coumarins and 2-Pyrones via a Double C-H Activation. Organic letters, 18(11), 2540-3. https://doi.org/10.1021/acs.orglett.6b00751
Mackey, Katrina, et al. "Cyclization of 4-Phenoxy-2-coumarins and 2-Pyrones via a Double C-H Activation." Organic letters vol. 18,11 (2016): 2540-3. doi: https://doi.org/10.1021/acs.orglett.6b00751
Mackey K, Pardo LM, Prendergast AM, Nolan MT, Bateman LM, McGlacken GP. Cyclization of 4-Phenoxy-2-coumarins and 2-Pyrones via a Double C-H Activation. Org Lett. 2016 Jun 03;18(11):2540-3. doi: 10.1021/acs.orglett.6b00751. Epub 2016 May 19. PMID: 27196033.
Copy Download .nbib Format: NLM
Share it on

Org Lett. 2016 Jun 03;18(11):2540-3. doi: 10.1021/acs.orglett.6b00751. Epub 2016 May 19.

Cyclization of 4-Phenoxy-2-coumarins and 2-Pyrones via a Double C-H Activation.

Organic letters

Katrina Mackey, Leticia M Pardo, Aisling M Prendergast, Marie-T Nolan, Lorraine M Bateman, Gerard P McGlacken

Affiliations

  1. Department of Chemistry and Analytical & Biological Chemistry Research Facility, University College Cork , College Road, Cork, Ireland.

PMID: 27196033 DOI: 10.1021/acs.orglett.6b00751

Abstract

Aryl-heteroaryl coupling via double C-H activation is a powerful transformation that avoids the installation of activating groups. A double C-H activation of privileged biological scaffolds, 2-coumarins and 2-pyrones, is reported. Despite the rich chemistry of these molecular frameworks, the yields are very good. Excellent regioselectivity was achieved on the pyrones. This methodology was applied to the synthesis of flemichapparin C in three steps. Isotope effect experiments were carried out, and a mechanism is proposed.

Publication Types