Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 23, Pages 9132-9139Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo9017827
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Funding
- National Institute of General Medical Sciences [GM070620]
- National Institutes of Health Kansas University Chemical Methodologies and Library Development Center of Excellence [P50 GM069663]
- National Science Foundation
- Johnson Matthey, Inc.
- Kawaken Fine Chemicals Co., Ltd.
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A number of functionally substituted 9-fluorenylidenes and 9,10-phenanthrenes have been synthesized from substituted o-halostyrenes and o-halo allylic benzenes respectively in good yields by the palladium-catalyzed annulation of arynes. The methodology tolerates a variety of functional groups, including cyano, ester, aldehyde, and ketone groups, occurs Under relatively mild reaction conditions, and involves the generation of two new carbon-carbon bonds, thus providing these important carbocyclic ring systems in a single synthetic step.
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