Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 4, Pages 1047-1060Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo902515z
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- NSERC
- University of Ottawa
- Astra Zeneca
- Amgen
- Eli Lilly
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Through the introduction of an aryl chloride substituent, the selectivity of palladium-catalyzed direct arylation may be diverted to provide alternative regioisomeric products in high yields. In cases where low reactivity is typically observed, the presence of the carbon-chlorine bond can serve to enhance reactivity and provide superior outcomes. From a strategic perspective, the C-Cl bond is easily introduced and can be employed in a variety of subsequent transformations to provide a wealth of highly functionalized heterocycles with minimal substrate preactivation. The impact of the C-Cl functional group on direct arylation reactivity has also been evaluated mechanistically, and the observed reactivity profiles correlate very well with that predicted by a concerted metalation-deprotonation pathway.
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