Journal
ACS COMBINATORIAL SCIENCE
Volume 14, Issue 7, Pages 403-414Publisher
AMER CHEMICAL SOC
DOI: 10.1021/co300040q
Keywords
solution-phase parallel synthesis; multisubstituted furans; 3-iodofurans; iodocyclization; electrophiles; nucleophiles
Funding
- National Institute of General Medical Sciences [GM070620, GM079593]
- National Institutes of Health Kansas University Center of Excellence for Chemical Methodologies and Library Development [GM069663]
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A library of furans has been synthesized by iodocyclization and further diversified by palladium-catalyzed coupling processes. The key intermediate 3-iodofurans have been prepared by the electrophilic iodocyclization of 2-iodo-2-alken-1-ones in the presence of various nucleophiles in good to excellent yields under mild reaction conditions. These 3-iodofurans are the key components for library generation through subsequent elaboration by palladium-catalyzed processes, such as Suzuki-Miyaura, Sonagashira, Heck, aminocarbonylation, and carboalkoxylation chemistry to afford a diverse set of 2,3,4,5-tetrasubstituted furans.
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