Journal
ORGANIC LETTERS
Volume 18, Issue 11, Pages 2540-2543Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00751
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Funding
- Science Foundation Ireland [SFI/12/IP/1315, SFI/12/RC/2275, 14/ADV/RC2751]
- Irish Research Council/Pfizer
- Science Foundation Ireland (SFI) [14/ADV/RC2751] Funding Source: Science Foundation Ireland (SFI)
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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.
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